WO2015134095A1 - Isolation thermique - Google Patents

Isolation thermique Download PDF

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Publication number
WO2015134095A1
WO2015134095A1 PCT/US2014/072198 US2014072198W WO2015134095A1 WO 2015134095 A1 WO2015134095 A1 WO 2015134095A1 US 2014072198 W US2014072198 W US 2014072198W WO 2015134095 A1 WO2015134095 A1 WO 2015134095A1
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WO
WIPO (PCT)
Prior art keywords
cyclic olefin
composition
mol
thermal insulation
substituted
Prior art date
Application number
PCT/US2014/072198
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English (en)
Inventor
Brian L. CONLEY
Anthony R. Stephen
Michael Giardello
Christopher J. Cruce
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Materia, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Priority claimed from PCT/US2014/043968 external-priority patent/WO2014210076A1/fr
Application filed by Materia, Inc. filed Critical Materia, Inc.
Priority to US15/122,860 priority Critical patent/US10711090B2/en
Publication of WO2015134095A1 publication Critical patent/WO2015134095A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • E—FIXED CONSTRUCTIONS
    • E21—EARTH OR ROCK DRILLING; MINING
    • E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
    • E21B36/00—Heating, cooling or insulating arrangements for boreholes or wells, e.g. for use in permafrost zones
    • E21B36/003—Insulating arrangements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3324—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from norbornene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/418—Ring opening metathesis polymerisation [ROMP]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/59—Stability
    • C08G2261/592—Stability against heat
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
    • F16L59/00—Thermal insulation in general
    • F16L59/14—Arrangements for the insulation of pipes or pipe systems
    • F16L59/16—Arrangements specially adapted to local requirements at flanges, junctions, valves or the like
    • F16L59/18—Arrangements specially adapted to local requirements at flanges, junctions, valves or the like adapted for joints
    • F16L59/20—Arrangements specially adapted to local requirements at flanges, junctions, valves or the like adapted for joints for non-disconnectable joints

Definitions

  • the present invention relates to the field of insulated pipelines and structures, particularly to the field of subsea pipelines and structures. More particularly, the present invention relates to thermal insulation materials and compositions for insulating offshore oil drilling equipment and structures, particularly subsea pipelines and structures. The present invention also relates to methods of using such thermal insulation materials and compositions to insulate offshore oil drilling equipment and structures, and articles of manufacture comprising such thermal insulation materials and compositions.
  • Offshore oil drilling requires the transportation of hydrocarbons from wellheads positioned underwater to shore or other surface equipment for further distribution. As temperature decreases the resistance to flow of liquids such as oil increases. Pipelines used in the transportation of oil from the underwater wellheads are generally insulated to avoid a substantial decrease in the temperature of the oil. Moreover, the underwater environment exposes pipelines and other oil drilling equipment to compressive forces, salt water corrosion, near-freezing water temperatures, possible water absorption, undersea currents, and marine life. Most pipes and pipelines used in offshore oil drilling are constructed of metal, typically some grade of steel.
  • thermal insulation materials have also become increasingly demanding. Recent advances in drilling technology and depletion of readily accessible sub- sea oil wells have resulted in the push toward deep water drilling where oil temperatures are typically hotter. This results in higher temperature pipelines and structures. Though several materials (e.g., polymer materials and/or polymer composite materials) with higher design temperatures have been developed, the peak use temperature of these materials has plateaued near 150 - 160 °C. Thus, a need exists for easily applied thermal insulation materials that pass the requisite qualification tests so as to be suitable for use on subsea and subterranean pipelines with maximum flowline operating temperatures (MFOTs) above 150 - 160 °C.
  • MFOTs flowline operating temperatures
  • thermal insulation materials in particular thermal insulation materials for subsea applications include: thermal stability above 175 °C; resistance to hydrolysis above 175 °C; flexibility greater than 5% elongation at break at 25 °C; compatibility with glass microspheres; fast cure times; low thermal conductivity; high impact strength; castable (high throughput with low capital expenditure cost); rigid for robust pipe handling without external protection; can be processed in air; can be applied in thick sections without multi-layering; can be applied to complex geometries; rapid full cure under production conditions; processable in the presence of trace moisture (water).
  • thermal insulation materials particularly thermal insulation materials for subsea applications (e.g., thermal insulation for pipe and pipelines and other subsea equipment and structures, such as coatings for field joints, etc.) that possess all of these desirable characteristics and/or properties.
  • Thermal stability as used herein means that a material maintains its structural integrity when subjected to elevated temperatures.
  • Polyurethanes have been used for insulating subsea pipelines and equipment due to somewhat general ease in processing and generally good mechanical properties.
  • polyurethane insulation may suffer from hydrolytic degradation when exposed to hot-wet environments.
  • hydrolytic degradation of the polyurethane polymer network particularly at elevated temperatures where water is able to ingress the polymer network, which would negatively affect the insulation capabilities of the polyurethane polymer.
  • Polypropylene is another polymer material that is used to insulate subsea pipelines and equipment.
  • the application of polypropylene is a more difficult process generally requiring extrusion of multiple layers.
  • polypropylene does not possess attractive thermal and mechanical properties.
  • Polystyrene is another polymer material that is used to insulate subsea pipelines and equipment, however, polystyrene does not possess attractive thermal and mechanical properties.
  • Another material used for insulating subsea pipelines and equipment is rigid epoxy syntactic foam, where hollow glass or ceramic spheres are combined with the epoxy resin.
  • This material possesses good thermal conductivity, but suffers from being very brittle and rigid, making this material susceptible to damage when exposed to high stress forces and/or sudden impacts. Moreover, these materials are difficult to remove and replace as they are attached to the surface mechanically or through the use of adhesives.
  • Silicones and syntactic silicones where hollow glass or ceramic spheres are combined with the silicones are another polymer material that is used to insulate subsea pipelines and equipment, however, silicones and syntactic silicones may suffer from hydrolytic degradation when exposed to hot wet environments. Moreover, silicones generally require long cure cycles.
  • Phenolics are another polymer material that is used to insulate subsea pipelines and equipment; however, phenolics are generally difficult to apply to such objects. These materials also suffer from being very brittle and rigid, making this material susceptible to damage when exposed to high stress forces and/or sudden impacts.
  • Another material for insulating subsea pipelines and equipment is elastomeric amine cured epoxy resins. While elastomeric amine cured epoxy resins may offer some advantages over
  • these materials possess several limitations, particularly in that at least two steps and specialized equipment are required to prepare such elastomeric amine cured epoxy resins. Moreover, these materials are viscous liquids (e.g., 90,000 cP at 25 °C), making the filling of complex molds difficult.
  • Rubber materials including silicone rubber, are examples of other materials used to insulate subsea pipelines and equipment. These materials do not possess attractive thermal and mechanical properties, and generally require long cure cycles, as well as having other limitations.
  • Dicyclopentadiene polymer (pDCPD) prepared from Telene® 1650 DCPD resin is another example of a material that has been reported for use as a field joint coating material, however, this material (including similar materials such as Metton® DCPD resin and Pentam® DCPD resin) possess several limitations, which are well known in the art .
  • Telene® 1650 DCPD resin (BF Goodrich/Telene SAS) and Metton® DCPD resin (Metton America/Hercules) are both based on a two component system comprising molybdenum (Telene SAS/BF Goodrich) or tungsten (Metton America/Hercules) pre-catalyst dissolved in DCPD monomer (B-component) and an aluminum alkyl or aluminum alkyl halide co-catalyst dissolved in DCPD monomer (A-component).
  • molybdenum and tungsten catalyzed DCPD resins are extremely sensitive to chemical functional groups and to air (oxygen) and moisture (water), even at trace levels.
  • DCPD monomer resins for use in molding of polymer articles typically contain between 0% -30% by weight of tricyclopentadiene, and lesser amounts of higher oligomers of cyclopentadiene such as tetramers and pentamers of cyclopentadiene (e.g.,
  • the present invention is directed to addressing one or more of the aforementioned concerns and relates to thermal insulation materials and thermal insulation material compositions and methods for thermally insulating pipelines and associated equipment, structures, and objects used in offshore drilling.
  • the present invention is also relates to articles of manufacture comprising the thermal insulation materials and/or thermal insulation material compositions of the invention.
  • ROMP polymers ring opening metathesis polymerization polymers
  • ROMP polymers and/or ROMP polymer composites of the invention offer several advantages over prior art materials used for thermally insulating pipelines and associated equipment, structures, and objects used in offshore oil drilling.
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 50.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 40.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 20.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 80.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 30.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a cyclic olefin composition comprising at least one cyclic olefin containing multiunsaturation, and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or
  • the invention provides a cyclic olefin composition comprising at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 50.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 50.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 40.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 10.0 mol% to 40.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 20.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 80.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 20.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 80.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 30.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 30.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 70.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 50.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z ) n -Fn where n is zero or 1, Z and Fn, and functional groups (Fn); and up to 60.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 50.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 70.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and up to 60.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl,
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl,
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z ) n -Fn where n is zero or 1, Z and Fn, and functional groups (Fn).
  • the invention provides a cyclic olefin composition comprising 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and 40.0 mol% to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl,
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 50.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 40.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 20.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 80.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 30.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises at least one cyclic olefin containing multiunsaturation, and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted.
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom- containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarby
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 50.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 50.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 40.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 40.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 20.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 80.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 20.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 80.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 30.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 30.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z ) n -Fn where n is zero or 1 , Z and Fn, and functional groups (Fn); and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and 40.0 mol% to 60.0 0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n - Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and 30.0 mol% to 60.0 0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n - Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 50.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a resin composition comprising a cyclic olefin composition, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and 40.0 mol% to 50.0 0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n - Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises a ROMP polymer.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises a ROMP polymer.
  • the thermal insulation material comprises a ROMP polymer.
  • the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises a ROMP polymer.
  • the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises a ROMP polymer composite.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises a ROMP polymer composite, wherein the ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises a ROMP polymer composite, wherein the ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst is used to thermally insulate any object from a surrounding environment.
  • the invention provides a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst is used to thermally insulate any object from a surrounding environment.
  • a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst is used to thermally insulate any object from a surrounding environment, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • ROMP polymer is used to thermally insulate any object from a surrounding environment.
  • a ROMP polymer is used to thermally insulate any object from a surrounding environment, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • a ROMP polymer is used to thermally insulate any object from a surrounding environment, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • ROMP polymer composite is used to thermally insulate any object from a surrounding environment.
  • a ROMP polymer composite is used to thermally insulate any object from a surrounding environment, wherein the ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • a ROMP polymer composite is used to thermally insulate any object from a surrounding environment, wherein the ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • a reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one olefin metathesis catalyst is used to thermally insulate objects, equipment, structures, systems used in offshore oil drilling.
  • a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one olefin metathesis catalyst is used to thermally insulate objects, equipment, structures, systems used in offshore oil drilling.
  • a reaction product of a resin composition comprising at a cyclic olefin composition and a catalyst composition comprising at least one olefin metathesis catalyst is used to thermally insulate objects, equipment, structures, systems used in offshore oil drilling, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • a reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst is used to thermally insulate undersea pipes and well head equipment from sea water.
  • a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst is used to thermally insulate undersea pipes and well head equipment from sea water.
  • a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst is used to thermally insulate undersea pipes and well head equipment from sea water, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, contacting the ROMP composition with a substrate material, subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer composite for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, contacting the ROMP composition with a substrate material, subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer composite for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, contacting the ROMP composition with a substrate material, subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer composite for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising at least one cyclic olefin and at least one substrate material with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer composite for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising a cyclic olefin composition and at least one substrate material with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer composite for use as a thermal insulation material.
  • thermal insulation materials of the invention are prepared by combining a resin composition comprising a cyclic olefin composition and at least one substrate material with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, thereby forming a ROMP polymer composite for use as a thermal insulation material.
  • a process for providing a ROMP polymer coating for offshore applications comprising, providing an object surface to be coated, providing a resin composition comprising at least one cyclic olefin, providing a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, combining the resin composition comprising at least one cyclic olefin and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, contacting the object surface with the ROMP composition, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition.
  • a process for providing a ROMP polymer coating for offshore applications comprising, providing an object surface to be coated, providing a resin composition comprising a cyclic olefin composition, providing a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, combining the resin composition comprising the cyclic olefin composition and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, contacting the object surface with the ROMP composition, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition.
  • a process for providing a ROMP polymer coating for offshore applications comprising, providing an object surface to be coated, providing a resin composition comprising a one cyclic olefin composition, providing a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, combining the resin composition comprising at least one cyclic olefin composition and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • ROMP composition multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, contacting the object surface with the ROMP composition, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition.
  • a process for providing a ROMP polymer coating for offshore applications comprising, providing an object surface to be coated, providing a resin composition comprising at least one cyclic olefin, providing a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, combining the resin composition comprising at least one cyclic olefin and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, applying the ROMP composition to the object surface, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition.
  • a process for providing a ROMP polymer coating for offshore applications comprising, providing an object surface to be coated, providing a resin composition comprising a cyclic olefin composition, providing a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, combining the resin composition comprising the cyclic olefin composition and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, applying the ROMP composition to the object surface, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition.
  • a process for providing a ROMP polymer coating for offshore applications comprising, providing an object surface to be coated, providing a resin composition comprising a one cyclic olefin composition, providing a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, combining the resin composition comprising at least one cyclic olefin composition and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst to form a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • the ROMP composition applying the ROMP composition to the object surface, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition.
  • the invention provides a thermal insulation material comprising a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises at least one cyclic olefin containing multiunsaturation, and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing
  • multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn, and functional groups (Fn); and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn).
  • the invention provides a thermal insulation material comprising a resin composition comprising a one cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 20.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 80.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 30.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 40.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 50.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 70.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 40.0 mol% to 70.0 mol% of at least one cyclic olefin containing multiunsaturation, and 30.0 mol% to 60.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 50.0 mol% to 60.0 mol% of at least one cyclic olefin containing multiunsaturation, and 40.0 mol% to 50.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material, comprising: a resin composition comprising at least one cyclic olefin; and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material, comprising: a resin composition comprising a cyclic olefin composition; and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material, comprising: a resin composition comprising a one cyclic olefin composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material, wherein the thermal insulation material comprises the reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material, wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material, wherein the thermal insulation material comprises the reaction product of a resin composition comprising at least one cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for subsea applications comprising a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for subsea applications comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for subsea applications comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • the invention provides a thermal insulation material for subsea applications, wherein the thermal insulation material comprises the reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for subsea applications, wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for subsea applications, wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a subsea thermal insulation material comprising a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a subsea thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises at least one cyclic olefin containing multiunsaturation, and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted.
  • the invention provides a subsea thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a subsea thermal insulation material, wherein the subsea thermal insulation material comprises the reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a subsea thermal insulation material, wherein the subsea thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a subsea thermal insulation material, wherein the subsea thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing
  • the invention provides a thermal insulation material, comprising a ROMP polymer or a ROMP polymer composite.
  • the invention provides a thermal insulation material, comprising a ROMP polymer or a ROMP polymer composite, wherein the ROMP polymer or ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material, comprising a ROMP polymer or a ROMP polymer composite, wherein the ROMP polymer or ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material for subsea applications, wherein the thermal insulation material comprises a ROMP polymer or a ROMP polymer composite.
  • the invention provides a thermal insulation material for subsea applications, wherein the thermal insulation material comprises a ROMP polymer or a ROMP polymer composite, wherein the ROMP polymer or ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for subsea applications, wherein the thermal insulation material comprises a ROMP polymer or a ROMP polymer composite, wherein the ROMP polymer or ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material composition comprising a resin composition comprising at least one cyclic olefin; and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material composition comprising a resin composition comprising a cyclic olefin composition; and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material composition
  • a resin composition comprising a cyclic olefin composition
  • the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good low temperature flexibility.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good low temperature flexibility, wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good low temperature flexibility, wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good low temperature flexibility.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good low temperature flexibility, wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good low temperature flexibility, wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good low temperature impact properties.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good low temperature impact properties, wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good low temperature impact properties, wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good low temperature impact properties.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good low temperature impact properties, wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good low temperature impact properties, wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good corrosion resistance to sea water (salt water).
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good corrosion resistance to sea water (salt water), wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good corrosion resistance to sea water (salt water), wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good corrosion resistance to sea water (salt water).
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good corrosion resistance to sea water (salt water), wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good corrosion resistance to sea water (salt water), wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good thermal conductivity (e.g., low k value).
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good thermal conductivity (e.g., low k value), wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer materials for use as thermal insulation materials, where the ROMP polymer materials have good thermal conductivity (e.g., low k value), wherein the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the ROMP polymer materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic o
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good thermal conductivity (e.g., low k value).
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good thermal conductivity (e.g., low k value), wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the present invention provides ROMP polymer composite materials for use as thermal insulation materials, where the ROMP polymer composites have good thermal conductivity (e.g., low k value), wherein the ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst
  • the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation,
  • the ROMP polymers and/or ROMP polymer composites of the invention may be applied to an object using a variety of methods known in the art.
  • a form or mold is placed or constructed around the object to be insulated.
  • the resin composition comprising at least one cyclic olefin and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst are combined to form a ROMP composition and the ROMP composition is the applied between the object and the mold and the ROMP composition is then subjected to conditions effective to cure the ROMP composition. Once the ROMP composition has cured, the mold is removed.
  • the ROMP polymers and/or ROMP polymer composites of the invention may be applied to an object using a variety of methods known in the art.
  • a form or mold is placed or constructed around the object to be insulated.
  • the resin composition comprising a cyclic olefin composition and the catalyst composition comprising at least one metal carbene olefin metathesis catalyst are combined to form a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, and the ROMP composition is the applied between the object and the mold and the ROMP composition is then subjected to conditions effective to cure the ROMP composition.
  • the ROMP polymer and/or ROMP polymer composite thermal insulation materials of the invention need not necessarily be molded around an object to be insulated.
  • a ROMP polymer article and/or ROMP polymer composite article may be independently prepared and then subsequently affixed to or placed around an object to thermally insulate the object from the surrounding environment.
  • the means for affixing a ROMP polymer article and/or ROMP polymer composite article to an object may be by any known means including an adhesive means and/or mechanical means such as fasteners, bolts, screws, etc.
  • a ROMP polymer thermal insulation material and/or a ROMP polymer composite thermal insulation material can be pre-made into sections which are shaped to complement the object to be insulated.
  • the pre-made sections may then be secured or affixed to the object using any known means, wherein the ROMP polymer and/or ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation
  • the ROMP polymer and/or ROMP polymer composite thermal insulation materials of the invention wherein the ROMP polymer and/or ROMP polymer composite thermal insulation materials are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • a ROMP polymer article and/or ROMP polymer composite article may be independently prepared and then subsequently affixed to or placed around an object to thermally insulate the object from the surrounding environment.
  • the means for affixing a ROMP polymer article and/or ROMP polymer composite article to an object may be by any known means including an adhesive means and/or mechanical means such as fasteners, bolts, screws, etc.
  • a ROMP polymer thermal insulation material and/or a ROMP polymer composite thermal insulation material can be pre-made into sections which are shaped to complement the object to be insulated.
  • the pre-made sections may then be secured or affixed to the object using any known means.
  • thermal insulation material compositions and/or ROMP polymer compositions and/or ROMP polymer composite compositions of the invention can be formulated so as to have a wide range of tunable cure times.
  • the thermal insulation material compositions and/or ROMP polymer compositions and/or ROMP polymer composite compositions of the invention can be formulated so as to have a wide range of tunable cure times, wherein the ROMP polymer compositions and/or ROMP polymer composite compositions comprise a resin composition comprising a cyclic olefin composition contacted with a catalyst composition comprising at least one metal carbene olefin metathesis catalysts.
  • the thermal insulation material compositions and/or ROMP polymer compositions and/or ROMP polymer composite compositions of the invention can be formulated so as to have a wide range of tunable cure times, wherein the ROMP polymer compositions and/or ROMP polymer composite compositions comprise a resin composition comprising a cyclic olefin composition contacted with a catalyst composition comprising at least one metal carbene olefin metathesis catalysts, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint, a subsea Christmas tree, jumper, spool piece, pipeline end termination, pipeline end manifold, robotic part, a robotic device, a robotic vehicle, wellhead equipment, a subsea dog house, or combinations thereof.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and at least one metal carbene olefin metathesis catalyst, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint, a subsea Christmas tree, jumper, spool piece, pipeline end termination, pipeline end manifold, robotic part, a robotic device, a robotic vehicle, wellhead equipment, a subsea dog house, or combinations thereof.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint, a subsea Christmas tree, jumper, spool piece, pipeline
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid where the thermal insulation material comprises a ROMP composition.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid where the thermal insulation material comprises a ROMP composition, wherein the ROMP composition comprises a resin composition comprising a cyclic olefin composition contacted with a catalyst composition comprising at least one metal carbene olefin metathesis catalysts.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid where the thermal insulation material comprises a ROMP composition, wherein the ROMP composition comprises a resin composition comprising a cyclic olefin composition contacted with a catalyst composition comprising at least one metal carbene olefin metathesis catalysts, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid where the thermal insulation material comprises a ROMP composition, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint, a subsea Christmas tree, jumper, spool piece, pipeline end termination, pipeline end manifold, robotic part, a robotic device, a robotic vehicle, wellhead equipment, a subsea dog house, or combinations thereof.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid where the thermal insulation material comprises a ROMP composition, wherein the ROMP composition comprises a resin composition comprising a cyclic olefin composition contacted with a catalyst composition comprising at least one metal carbene olefin metathesis catalysts, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint, a subsea Christmas tree, jumper, spool piece, pipeline end termination, pipeline end manifold, robotic part, a robotic device, a robotic vehicle, wellhead equipment, a subsea dog house, or combinations thereof.
  • the thermal insulation material comprises a ROMP composition
  • the ROMP composition comprises
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid where the thermal insulation material comprises a ROMP composition, wherein the ROMP composition comprises a resin composition comprising a cyclic olefin composition contacted with a catalyst composition comprising at least one metal carbene olefin metathesis catalysts, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint,
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid, where the thermal insulation material comprises a ROMP polymer.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid, where the thermal insulation material comprises a ROMP polymer, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid, where the thermal insulation material comprises a ROMP polymer, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid, where the thermal insulation material comprises a ROMP polymer, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint, a subsea Christmas tree, jumper, spool piece, pipeline end termination, pipeline end manifold, robotic part, a robotic device, a robotic vehicle, wellhead equipment, a subsea dog house, or combinations thereof.
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid, where the thermal insulation material comprises a ROMP polymer, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold, riser, field joint, a subsea Christmas tree, jumper, spool piece, pipeline end termination, pipeline end manifold, robotic part, a robotic device, a robotic vehicle, wellhead equipment, a subsea dog house, or combinations thereof.
  • the thermal insulation material comprises a ROMP polymer
  • the invention provides a method of thermally insulating an object from a surrounding fluid, the method comprising interposing a thermal insulation material between the object and the fluid, where the thermal insulation material comprises a ROMP polymer, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the interposition of the thermal insulation material is achieved by positioning a mold a predetermined distance from the object and applying the thermal insulation material between the object and the mold, wherein the object is a pipe, pipeline, pipe fitting, hose, hose fitting, tank, container, drum, manifold,
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing
  • thermo insulation material composition applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a thermal insulation material composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; applying the thermal insulation material composition to the at least a portion of at least one surface of the object; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; contacting the ROMP composition with at least a portion of at least one surface of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP
  • the invention provides a method for encasing an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition; contacting the ROMP composition with the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; contacting the ROMP composition with the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; contacting the ROMP composition with the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising at least one cyclic olefin with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition; applying the ROMP composition to the at least a portion of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the at least one cyclic olefin in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; applying the ROMP composition to the at least a portion of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for encasing at least a portion of an object with a thermal insulation material, comprising: combining a resin composition comprising a cyclic olefin composition with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, thereby forming a ROMP composition, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation; applying the ROMP composition to the at least a portion of the object; and subjecting the ROMP composition to conditions effective to promote a ROMP reaction of the cyclic olefin composition in the presence of the at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material is a ROMP polymer or a ROMP polymer composite.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, wherein the thermal insulation material is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a method for coating at least a portion of at least one surface of an object with a thermal insulation material, wherein the thermal insulation material is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • a process for applying a thermal insulation material composition to a pipe comprising:; placing a mold around a pipe to define a cavity between an internal surface of the mold and the pipe; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction between the at least one cyclic olefin and the at least one metal carbene olefin metathesis catalyst.
  • a process for applying a thermal insulation material composition to a pipe comprising:; placing a mold around a pipe to define a cavity between an internal surface of the mold and the pipe; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction between the cyclic olefin composition and the at least one metal carbene olefin metathesis catalyst.
  • a process for applying a thermal insulation material composition to a pipe comprising:; placing a mold around a pipe to define a cavity between an internal surface of the mold and the pipe; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • a process for applying a thermal insulation material composition to an object comprising: placing a mold around an object to define a cavity between an internal surface of the mold and the object; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction between the at least one cyclic olefin and the at least one metal carbene olefin metathesis catalyst.
  • a process for applying a thermal insulation material composition to an object comprising: placing a mold around an object to define a cavity between an internal surface of the mold and the object; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction between the cyclic olefin composition and the at least one metal carbene olefin metathesis catalyst.
  • a process for applying a thermal insulation material composition to an object comprising: placing a mold around an object to define a cavity between an internal surface of the mold and the object; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the thermal insulation material composition comprises a resin composition comprising at least one cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing
  • thermo insulation material composition comprising: monounsaturation; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction between the at least one cyclic olefin and the at least one metal carbene olefin metathesis catalyst.
  • a process for applying a thermal insulation material composition to a field joint comprising:; placing a mold around a field joint to define a cavity between an internal surface of the mold and the field joint; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction between the at least one cyclic olefin and the at least one metal carbene olefin metathesis catalyst.
  • a process for applying a thermal insulation material composition to a field joint comprising:; placing a mold around a field joint to define a cavity between an internal surface of the mold and the field joint; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst; and subjecting the thermal insulation material composition to conditions effective to promote a ROMP reaction between the cyclic olefin composition and the at least one metal carbene olefin metathesis catalyst.
  • a process for applying a thermal insulation material composition to a field joint comprising:; placing a mold around a field joint to define a cavity between an internal surface of the mold and the field joint; injecting a thermal insulation material composition in the cavity, wherein the thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • the invention provides an object at least partially encased by a thermal insulation material, wherein the thermal insulation material comprises the reaction product of at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst.
  • the invention provides an object at least partially encased by a thermal insulation material, wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides an object at least partially encased by a thermal insulation material, wherein the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides an object at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP composition.
  • the invention provides an object at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP composition, wherein the ROMP composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides an object at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP composition, wherein the ROMP composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the thermal insulation material comprises a ROMP composition
  • the ROMP composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst
  • the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation,
  • the invention provides an object at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite.
  • the invention provides an object at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides an object at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a pipe at least partially encased by a thermal insulation material, where the thermal insulation material comprises the reaction product of at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst.
  • the invention provides a pipe at least partially encased by a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a pipe at least partially encased by a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a pipe at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite.
  • the invention provides a pipe at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a pipe at least partially encased by a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises the reaction product of at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation .
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially coated with a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a field joint at least partially encased with a thermal insulation material, where the thermal insulation material comprises the reaction product of at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially encased with a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially encased with a thermal insulation material, where the thermal insulation material comprises the reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a field joint at least partially encased with a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite.
  • the invention provides a field joint at least partially encased with a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a field joint at least partially encased with a thermal insulation material, where the thermal insulation material comprises a ROMP polymer or ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides a thermal insulation material for use in coating a field joint, the thermal insulation material comprising a resin composition comprising at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for use in coating a field joint, the thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for use in coating a field joint, the thermal insulation material comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing
  • the invention provides a thermal insulation material for use in coating an object, the thermal insulation material comprising a resin composition comprising at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for use in coating an object, the thermal insulation material comprising a resin composition comprising cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides a thermal insulation material for use in coating an object, the thermal insulation material comprising a resin composition comprising cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing
  • the invention provides for use of at least one thermal insulation material composition for coating at least a portion of at least one surface of an object, wherein the at least one thermal insulation material composition comprises a resin composition comprising at least one cyclic olefin and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides for use of at least one thermal insulation material composition for coating at least a portion of at least one surface of an object, wherein the at least one thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides for use of at least one thermal insulation material composition for coating at least a portion of at least one surface of an object, wherein the at least one thermal insulation material composition comprises a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing
  • the invention provides for use of at least one thermal insulation material for coating at least a portion of at least one surface of an object, wherein the at least one thermal insulation material comprises a ROMP polymer or a ROMP polymer composite.
  • the invention provides for use of at least one thermal insulation material for coating at least a portion of at least one surface of an object, wherein the at least one thermal insulation material comprises a ROMP polymer or a ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides for use of at least one thermal insulation material for coating at least a portion of at least one surface of an object, wherein the at least one thermal insulation material comprises a ROMP polymer or a ROMP polymer composite, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • the invention provides an article of manufacture comprising an object, wherein at least a portion of at least one surface of the object is coated with a ROMP polymer, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst.
  • the invention provides an article of manufacture comprising an object, wherein at least a portion of at least one surface of the object is coated with a ROMP polymer, wherein the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing
  • the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted.
  • the invention provides for articles of manufacture made by any of the methods described herein.
  • FIG. 1 shows a pipe coated with a thermal insulation material comprising a ROMP polymer of Example 2, where an exposed section of the pipe is simulating a field joint.
  • FIG. 2 shows a pipe coated with a thermal insulation material comprising a ROMP polymer of Example 2, where the previously exposed section of the pipe simulating a field joint (FIG. 1) is now coated with (encased by) a thermal insulation material comprising a ROMP polymer of Example 2.
  • FIG. 3 is a graph of a cure profile of a ROMP composition (thermal insulation composition) applied to Pipe Sample (B).
  • alkyl refers to a linear, branched, or cyclic saturated hydrocarbon group typically although not necessarily containing 1 to about 24 carbon atoms, preferably 1 to about 12 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, ?-butyl, octyl, decyl, and the like, as well as cycloalkyl groups such as cyclopentyl, cyclohexyl, and the like. Generally, although again not necessarily, alkyl groups herein contain 1 to about 12 carbon atoms.
  • lower alkyl refers to an alkyl group of 1 to 6 carbon atoms
  • cycloalkyl refers to a cyclic alkyl group, typically having 4 to 8, preferably 5 to 7, carbon atoms.
  • substituted alkyl refers to alkyl substituted with one or more substituent groups
  • heteroatom-containing alkyl and “heteroalkyl” refer to alkyl in which at least one carbon atom is replaced with a heteroatom. If not otherwise indicated, the terms “alkyl” and “lower alkyl” include linear, branched, cyclic, unsubstituted, substituted, and/or heteroatom-containing alkyl and lower alkyl, respectively.
  • alkylene refers to a difunctional linear, branched, or cyclic alkyl group, where "alkyl” is as defined above.
  • alkenyl refers to a linear, branched, or cyclic hydrocarbon group of 2 to about 24 carbon atoms containing at least one double bond, such as ethenyl, «-propenyl, isopropenyl, n-butenyl, isobutenyl, octenyl, decenyl, tetradecenyl, hexadecenyl, eicosenyl, tetracosenyl, and the like.
  • Preferred alkenyl groups herein contain 2 to about 12 carbon atoms.
  • lower alkenyl refers to an alkenyl group of 2 to 6 carbon atoms
  • cycloalkenyl refers to a cyclic alkenyl group, preferably having 5 to 8 carbon atoms.
  • substituted alkenyl refers to alkenyl substituted with one or more substituent groups
  • heteroatom-containing alkenyl and “heteroalkenyl” refer to alkenyl in which at least one carbon atom is replaced with a heteroatom. If not otherwise indicated, the terms “alkenyl” and “lower alkenyl” include linear, branched, cyclic, unsubstituted, substituted, and/or heteroatom-containing alkenyl and lower alkenyl, respectively.
  • alkenylene refers to a difunctional linear, branched, or cyclic alkenyl group, where "alkenyl” is as defined above.
  • alkynyl refers to a linear or branched hydrocarbon group of 2 to about 24 carbon atoms containing at least one triple bond, such as ethynyl, «-propynyl, and the like. Preferred alkynyl groups herein contain 2 to about 12 carbon atoms. The term “lower alkynyl” refers to an alkynyl group of 2 to 6 carbon atoms.
  • substituted alkynyl refers to alkynyl substituted with one or more substituent groups
  • heteroatom-containing alkynyl and “heteroalkynyl” refer to alkynyl in which at least one carbon atom is replaced with a heteroatom.
  • alkynyl and “lower alkynyl” include linear, branched, unsubstituted, substituted, and/or heteroatom-containing alkynyl and lower alkynyl, respectively.
  • alkoxy refers to an alkyl group bound through a single, terminal ether linkage; that is, an "alkoxy” group may be represented as -O-alkyl where alkyl is as defined above.
  • a "lower alkoxy” group refers to an alkoxy group containing 1 to 6 carbon atoms.
  • alkenyloxy and lower alkenyloxy respectively refer to an alkenyl and lower alkenyl group bound through a single, terminal ether linkage
  • alkynyloxy and “lower alkynyloxy” respectively refer to an alkynyl and lower alkynyl group bound through a single, terminal ether linkage.
  • aryl refers to an aromatic substituent containing a single aromatic ring or multiple aromatic rings that are fused together, directly linked, or indirectly linked (such that the different aromatic rings are bound to a common group such as a methylene or ethylene moiety).
  • Preferred aryl groups contain 5 to 24 carbon atoms, and particularly preferred aryl groups contain 5 to 14 carbon atoms.
  • Exemplary aryl groups contain one aromatic ring or two fused or linked aromatic rings, e.g., phenyl, naphthyl, biphenyl, diphenylether, diphenylamine, benzophenone, and the like.
  • Substituted aryl refers to an aryl moiety substituted with one or more substituent groups
  • heteroatom-containing aryl and “heteroaryl” refer to aryl substituents in which at least one carbon atom is replaced with a heteroatom, as will be described in further detail infra.
  • aryloxy refers to an aryl group bound through a single, terminal ether linkage, wherein "aryl” is as defined above.
  • An "aryloxy” group may be represented as -O-aryl where aryl is as defined above.
  • Preferred aryloxy groups contain 5 to 24 carbon atoms, and particularly preferred aryloxy groups contain 5 to 14 carbon atoms.
  • aryloxy groups include, without limitation, phenoxy, o-halo-phenoxy, m-halo-phenoxy, p-halo-phenoxy, o-methoxy-phenoxy, m- methoxy-phenoxy, p-methoxy-phenoxy, 2,4-dimethoxy-phenoxy, 3,4,5-trimethoxy-phenoxy, and the like.
  • alkaryl refers to an aryl group with an alkyl substituent
  • aralkyl refers to an alkyl group with an aryl substituent, wherein “aryl” and “alkyl” are as defined above.
  • Alkaryl groups contain 6 to 24 carbon atoms, and particularly preferred alkaryl and aralkyl groups contain 6 to 16 carbon atoms.
  • Alkaryl groups include, without limitation, p-methylphenyl, 2,4-dimethylphenyl, p-cyclohexylphenyl, 2,7-dimethylnaphthyl, 7-cyclooctylnaphthyl, 3-ethyl- cyclopenta-l,4-diene, and the like.
  • aralkyl groups include, without limitation, benzyl, 2- phenyl-ethyl, 3 -phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4-benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.
  • alkaryloxy and “aralkyloxy” refer to substituents of the formula -OR wherein R is alkaryl or aralkyl, respectively, as just defined.
  • acyl refers to substituents having the formula -(CO)-alkyl, -(CO)-aryl, -(CO)- aralkyl, -(CO)-alkaryl, -(CO)-alkenyl, or -(CO)-alkynyl
  • acyloxy refers to substituents having the formula -0(CO)-alkyl, -0(CO)-aryl, -0(CO)-aralkyl, -0(CO)-alkaryl, -0(CO)-alkenyl, - 0(CO)-alkynyl wherein "alkyl,” “aryl,” “aralkyl”, alkaryl, alkenyl, and alkynyl are as defined above.
  • cyclic and ring refer to alicyclic or aromatic groups that may or may not be substituted and/or heteroatom containing, and that may be monocyclic, bicyclic, or polycyclic.
  • alicyclic is used in the conventional sense to refer to an aliphatic cyclic moiety, as opposed to an aromatic cyclic moiety, and may be monocyclic, bicyclic, or polycyclic.
  • halo and halogen are used in the conventional sense to refer to a chloro, bromo, fluoro, or iodo substituent.
  • Hydrocarbyl refers to univalent hydrocarbyl radicals containing 1 to about 30 carbon atoms, preferably 1 to about 24 carbon atoms, most preferably 1 to about 12 carbon atoms, including linear, branched, cyclic, saturated, and unsaturated species, such as alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and the like.
  • lower hydrocarbyl intends a hydrocarbyl group of 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms
  • hydrocarbylene refers to a divalent hydrocarbyl moiety containing 1 to about 30 carbon atoms, preferably 1 to about 24 carbon atoms, most preferably 1 to about 12 carbon atoms, including linear, branched, cyclic, saturated, and unsaturated species.
  • lower hydrocarbylene refers to a hydrocarbylene group of 1 to 6 carbon atoms.
  • Substituted hydrocarbyl refers to hydrocarbyl substituted with one or more substituent groups
  • heteroatom-containing hydrocarbyl and heterohydrocarbyl refer to hydrocarbyl in which at least one carbon atom is replaced with a heteroatom
  • substituted hydrocarbylene refers to hydrocarbylene substituted with one or more substituent groups
  • heteroatom-containing hydrocarbylene and “heterohydrocarbylene” refer to hydrocarbylene in which at least one carbon atom is replaced with a heteroatom.
  • hydrocarbyl and hydrocarbylene are to be interpreted as including substituted and/or heteroatom-containing hydrocarbyl and heteroatom- containing hydrocarbylene moieties, respectively.
  • heteroatom-containing refers to a hydrocarbon molecule or a hydrocarbyl molecular fragment in which one or more carbon atoms is replaced with an atom other than carbon, e.g., nitrogen, oxygen, sulfur, phosphorus, or silicon, typically nitrogen, oxygen, or sulfur.
  • heteroalkyl refers to an alkyl substituent that is heteroatom-containing
  • heterocyclic refers to a cyclic substituent that is heteroatom- containing
  • heteroaryl and “heteroaromatic” respectively refer to “aryl” and “aromatic” substituents that are heteroatom-containing, and the like.
  • heterocyclic group or compound may or may not be aromatic, and further that “heterocycles” may be monocyclic, bicyclic, or polycyclic as described above with respect to the term "aryl.”
  • heteroalkyl groups include without limitation alkoxyaryl, alkylsulfanyl-substituted alkyl, N-alkylated amino alkyl, and the like.
  • heteroaryl substituents include without limitation pyrrolyl, pyrrolidinyl, pyridinyl, quinolinyl, indolyl, pyrimidinyl, imidazolyl, 1 ,2,4-triazolyl, tetrazolyl, etc.
  • heteroatom- containing alicyclic groups include without limitation pyrrolidino, morpholino, piperazino, piperidino, etc.
  • substituted as in “substituted hydrocarbyl,” “substituted alkyl,” “substituted aryl,” and the like, as alluded to in some of the aforementioned definitions, is meant that in the hydrocarbyl, alkyl, aryl, or other moiety, at least one hydrogen atom bound to a carbon (or other) atom is replaced with one or more non-hydrogen substituents.
  • substituents include, without limitation: functional groups referred to herein as "Fn,” such as halo, hydroxyl, sulfhydryl, C1-C24 alkoxy, C2-C24 alkenyloxy, C2-C24 alkynyloxy, C5-C24 aryloxy, C6-C24 aralkyloxy, C6-C24 alkaryloxy, acyl (including C2-C24 alkylcarbonyl (-CO-alkyl) and C6-C24 arylcarbonyl (-CO-aryl)), acyloxy (-O-acyl, including C2-C24 alkylcarbonyloxy (-O-CO-alkyl) and C6-C24 arylcarbonyloxy (-O-CO-aryl)), C2-C24 alkoxycarbonyl (- (CO)-O-alkyl), C 6 -C 24 aryloxycarbonyl (-(CO)-aryl), halocarbonyl (Fn,” such
  • C2 -C 24 alkenyl (preferably C 2 -G 2 alkenyl, more preferably i- e alkenyl), C 2 -C 24 alkynyl (preferably C 2 -Ci 2 alkynyl, more preferably i- e alkynyl), C5- C 24 aryl (preferably Cs-Ci 4 aryl), C6-C 24 alkaryl (preferably C6-C16 alkaryl), and C6-C 24 aralkyl (preferably C6-C16 aralkyl).
  • “functionalized olefin,” “functionalized cyclic olefin,” and the like, is meant that in the hydrocarbyl, alkyl, olefin, cyclic olefin, or other moiety, at least one hydrogen atom bound to a carbon (or other) atom is replaced with one or more functional groups such as those described hereinabove.
  • “functional group” is meant to include any functional species that is suitable for the uses described herein. In particular, as used herein, a functional group would necessarily possess the ability to react with or bond to corresponding functional groups on a substrate surface.
  • the aforementioned functional groups may, if a particular group permits, be further substituted with one or more additional functional groups or with one or more hydrocarbyl moieties such as those specifically mentioned above.
  • the above-mentioned hydrocarbyl moieties may be further substituted with one or more functional groups or additional hydrocarbyl moieties as noted above.
  • substrate material is intended to generally mean any material that the resin compositions of the invention may be contacted with, applied to, or have the substrate material incorporated in to the resin.
  • such materials include reinforcing materials, such as filaments, fibers, rovings, mats, weaves, fabrics, knitted material, cloth or other known structures, glass fibers and fabrics, carbon fibers and fabrics, aramid fibers and fabrics, and polyolefin or other polymer fibers or fabrics.
  • a ROMP polymer composite may be comprised of one substrate material or a mixture of different substrate materials.
  • polymer backbone is intended to mean the chains of atoms in a polymer that comprise the main chain and any crosslinks, if it is a crosslinked polymer.
  • field joint is intended to generally mean a connection between adjoining members or parts, made at the time of installation (i.e. in the field).
  • field joint is a term of art often used to describe the welded ends of individual lengths of pipe.
  • pipelines used to transport oil and/or gas is most often formed from many individual pieces of pipe, for example steel pipe.
  • an anti-corrosion coating is often applied to the exterior surface of the pipe in such a manner that the exterior surface of the pipe ends remains uncoated.
  • the pipe may be subsequently coated with an insulation material;
  • the pipeline is formed by connecting the individual pieces of pipe by welding together the uncoated pipe ends. At least part of this welding process may take place at an onshore facility prior to loading the pipe on a lay barge or reel ship, with the remainder of the connections made offshore prior to the pipeline being deployed in offshore use.
  • an anti-corrosion coating may be applied to the exterior surface of the pipe in such a manner that the exterior surface of the pipe ends are also coated. In this instance, the anti-corrosion coating must be removed from the pipe ends prior to welding.
  • octyl norbornene and/or the abbreviation “ONB” refers to 5-octyl- 2-norbornene including endo/exo stereoisomers, and mixtures thereof.
  • tolyl norbornene and/or the abbreviation “Tolyl-NB” refers to 5-tolyl-2-norbornene including endo/exo stereoisomers, as well as para, ortho, and/or meta structural isomers, and mixtures thereof.
  • the term “decyl norbornene” and/or the abbreviation “DNB” refers to 5-decyl-2-norbornene including endo/exo stereoisomers, and mixtures thereof.
  • the term “hexyl norbornene” and/or the abbreviation “HNB” refers to 5-hexyl-2-norbornene including endo/exo stereoisomers, and mixtures thereof.
  • the term “phenyl norbornene” and/or the abbreviation “Phenyl-NB” refers to 5-phenyl-2-norbornene including endo/exo stereoisomers, and mixtures thereof.
  • weight percent (wt%) can be represented by gas chromatography (GC) percent area (area %). Hence, GC area% obtained from the GC was reported as wt%. Weight percent (wt%) and percent by weight are used interchangeably herein. Mol percent (mol%) was calculated from the weight percent (wt%) as is known in the art.
  • the present invention is directed to addressing one or more of the aforementioned concerns and relates to thermal insulation materials and thermal insulation material compositions and methods for thermally insulating pipelines and associated equipment, structures, and objects used in offshore drilling.
  • the present invention is also relates to articles of manufacture comprising the thermal insulation materials and/or thermal insulation material compositions of the invention.
  • thermal insulation materials and/or thermal insulation material compositions and/or ROMP polymer and/or ROMP polymer compositions of the present invention would possess all of the desired characteristics and/or properties specified above for thermal insulation materials, in particular thermal insulation materials used in offshore drilling (e.g. subsea applications).
  • the thermal insulation materials and/or thermal insulation material compositions and/or ROMP polymer and/or ROMP polymer compositions of the present invention disclosed herein satisfy this need in the industry, where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation.
  • ROMP polymers and/or ROMP polymer composites where the ROMP polymer or ROMP polymer composite are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation offer improved thermal stability and/or improved hydrolytic stability over prior art thermal insulation materials.
  • thermal insulation materials made from ROMP polymers where the ROMP polymer or is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, offer an advantage over prior art thermal insulation materials made from polypropylene in such ROMP polymers possess improved thermal stability.
  • thermal insulation materials made from ROMP polymers where the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • multiunsaturation and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation offer an advantage over prior art thermal insulation materials made from polyurethane and epoxy based materials, including elastomeric amine cured epoxy materials, in that cyclic olefins (cyclic olefin monomers) used to make such ROMP polymers may be selected so that the resultant ROMP polymers do not contain carbon- heteroatom bonds in the polymer backbone.
  • ROMP polymers where the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation are generally more hydrolytically stable than polyurethanes and/or epoxy based polymers, each of which possess carbon-heteroatom bonds in the polymer backbone.
  • ROMP polymers where the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, possess a polymer backbone containing only carbon-carbon single bonds and carbon-carbon double bonds, where the carbon atoms may be substituted or unsubstituted.
  • ROMP compositions of the invention used to prepare ROMP polymers and/or ROMP polymer composites where the ROMP polymers and/or ROMP polymer composites are a reaction product of a ROMP composition, the ROMP composition comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, are generally less sensitive to air and/or moisture than resins used to prepare polyurethane and epoxy based polymers and DCPD polymers prepared from molybdenum and tungsten catalyzed DCPD resins (e.g., Telene® DCPD Resin, Metton® DCPD
  • ROMP compositions comprising resin compositions comprising cyclic olefin compositions, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, and catalyst compositions comprising at least one metal carbene olefin metathesis catalyst are generally more robust to a wider array of environmental conditions (e.g., temperature, humidity, etc.) Resin systems that are less sensitive to air and/or moisture offer a benefit over more sensitive resin systems, particularly if objects are to be coated (thermally insulated) at on-site marine environments, such as on boats, offshore oil rigs, offshore oil platforms, etc.
  • environmental conditions e.g., temperature, humidity, etc.
  • ROMP polymers of the invention where the ROMP polymer is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation may be optionally hydrogenated by any known method, to provide a hydrogenated ROMP polymer for use as thermal insulation.
  • ROMP compositions of the invention comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, offer improved ease of application over prior art resin compositions, particularly polypropylene systems.
  • the ROMP composition comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, can be applied to an object and/or object surface by a variety of means including but not limited to pouring, casting, infusing, injecting, molding, spraying, rotationally molding, centrifugally casting, pultrusion, extrusion, etc.
  • ROMP compositions of the invention comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, also offer improved ease of application over prior art resin compositions based on epoxy resins (e.g., elastomeric amine cured epoxy materials).
  • epoxy resins e.g., elastomeric amine cured epoxy materials
  • the ROMP composition comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, simply require a single mixing step (e.g.
  • a resin composition comprising a cyclic olefin composition is mixed with a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation ) prior to application to an object surface or addition to a mold.
  • cyclic olefin compositions and/or resin compositions and/or ROMP compositions of the invention comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation can be applied to an object and/or object surface by a variety of means including but not limited to simple casting.
  • ROMP compositions of the invention comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, possess much lower viscosity over a broader range of temperatures than epoxy based resin systems.
  • the low viscosity of ROMP compositions of the invention comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, is particularly advantageous as it promotes flow especially when filling complex molds.
  • the low viscosity of cyclic olefin resin compositions also allows for high loading of substrate materials (e.g.
  • Suitable resin compositions for use with this invention having a viscosity at 25 °C ranging from about 1 centipoise to about 200 centipoise (1 cP - 200 cP). Viscosities typically range from 1- 150 cP, 1-100 cP, 5-100 cP, 5-150 cP, 5-25 cP, 5-50 cP, 5-15 cP, 5-20 cP at 25 °C.
  • viscosities may range from 1-150 cP, 1-100 cP, 5-100 cP, 5-150 cP, 5-25 cP, 5-50 cP, 5- 15 cP, 5-20 cP.
  • the ROMP composition comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, is that these compositions are easy to handle and can be easily formulated such that the resultant ROMP polymer(s) meet the
  • ROMP compositions the ROMP composition comprising a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing
  • ROMP polymers of the invention can be easily formulated such that the resultant ROMP polymer(s) may exhibit a range of physical, mechanical and/or thermal properties spanning the range from elastomeric behavior and/or properties to rigid thermoset behavior and/or properties depending on the needs/requirements of the application.
  • ROMP polymers and/or ROMP polymer composites of the present invention where the ROMP polymer and/or ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation can be used to thermally insulate any object from a surrounding environment or surrounding material, where the surrounding environment or surrounding material may be a gas (e.g.
  • ROMP polymers and/or ROMP polymer composites of the present invention where the ROMP polymer and/or ROMP polymer composite is a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation are suitable for thermal insulation of objects, such as oil pipelines in cold water (e.g.
  • ROMP polymers and/or ROMP polymer composites of the present invention where the ROMP polymers and/or ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation may be used to construct thermal insulation structures such as
  • ROMP polymers and/or ROMP polymer composites of the invention where the ROMP polymers and/or ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation are well suited for coating objects which are to be submerged in water (e.g. fresh water, salt water, sea water, etc.) the ROMP polymers and/or ROMP polymer composites may also be used to coat objects which are not exposed to an aqueous environment.
  • the ROMP polymers and/or ROMP polymer composites may also be used to coat objects which are not exposed to an aqueous environment
  • ROMP polymers and/or ROMP polymer composites of the present invention where the ROMP polymers and/or ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation may be used for coating (insulating) objects (e.g., pipes and/or other subsea structures) where the temperature of materials (e.g., hydrocarbons, oil, gas, etc.) transported by the objects (e.g., pipes and/or other structures) is greater than or equal to 160 °C.
  • insulating objects e.g., pipes and/or other subsea structures
  • ROMP polymers and/or ROMP polymer composites of the present invention where the ROMP polymers and/or ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation of the present invention may also be used for coating (insulating) objects (e.g., pipes and/or other subsea structures) where the temperature of materials (e.g., hydrocarbons, oil, gas, etc.) transported by the objects (e.g., pipes and/or other subsea structures) is less than 160 °C.
  • insulating e.g., pipes and/or other subse
  • ROMP polymers and/or ROMP polymer composites of the present invention where the ROMP polymers and/or ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation of the present invention have thermal conductivity values of less than 0.180 W/m*K, as determined by ASTM C518, as tested on heat flow instrument (FOX-50, LaserComp).
  • ROMP polymers and/or ROMP polymer composites of the present invention where the ROMP polymers and/or ROMP polymer composites are a reaction product of a resin composition comprising a cyclic olefin composition and a catalyst composition comprising at least one metal carbene olefin metathesis catalyst, wherein the cyclic olefin composition comprises 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation of the present invention may be further reduced by the addition of glass microspheres.
  • Adhesion promoters that may be used in the present invention disclosed herein are generally compounds containing at least two isocyanate groups (such as, for example, methylene diphenyl diisocyanate and hexamethylene diisocyanate).
  • the adhesion promoter may be a diisocyanate, triisocyanate, or polyisocyanate (i.e., containing four or more isocyanate groups).
  • the adhesion promoter may be a mixture of at least one diisocyanate, triisocyanate, or polyisocyanate.
  • the adhesion promoter comprises, or is limited to, a diisocyanate compound, or mixtures of diisocyanate compounds.
  • adhesion promoters that may be used in the present invention may be any compound having at least two isocyanate groups.
  • Suitable adhesion promoters include, without limitation, isocyanate compounds comprising at least two isocyanate groups, and wherein the compounds are selected from hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functionalized hydrocarbyl compounds.
  • suitable hydrocarbyl adhesion promoter compounds generally include alkyl, cycloalkyl, alkylene, alkenyl, alkynyl, aryl, cycloalkyl, alkaryl, and aralkyl compounds.
  • Substituted heteroatom-containing, and functionalized hydrocarbyl adhesion promoter compounds include the afore-mentioned hydrocarbyl compounds, as well as the variations thereof noted hereinabove.
  • Adhesion promoters that may be used in the present invention may be an alkyl diisocyanate.
  • An alkyl diisocyanate refers to a linear, branched, or cyclic saturated or unsaturated hydrocarbon group typically although not necessarily containing 1 to about 24 carbon atoms, preferably a diisocyanate containing 2 to about 12 carbon atoms, and more preferably a diisocyanate containing 6 to 12 carbon atoms such as hexamethylene diisocyanate (HDI), octamethylene diisocyanate, decamethylene diisocyanate, and the like.
  • Cycloalkyl diisocyanates contain cyclic alkyl group, typically having 4 to 16 carbon atoms.
  • a preferred cycloalkyl diisocyanate containing 6 to about 12 carbon atoms are cyclohexyl, cyclooctyl, cyclodecyl, and the like.
  • a more preferred cycloalkyl diisocyanate originates as a condensation product of acetone called 5-isocyanato-l-(isocyanatomethyl)- l,3,3-trimethyl-cyclohexane, commonly known as Isophorone diisocyanate (IPDI) and the isomers of isocyanato- [(isocyanatocyclohexyl)methyl]cyclohexane (H12MDI).
  • H12MDI is derived from the hydrogenated form of the aryl diisocyanate methylene diphenyl diisocyanate (MDI).
  • Adhesion promoters that may be used in the present invention may be an aryl diisocyanate.
  • Aryl diisocyanates refers to aromatic diisocyanates containing a single aromatic ring or multiple aromatic rings that are fused together, directly linked, or indirectly linked (such that the different aromatic rings are bound to a common group such as a methylene or ethylene moiety).
  • Preferred aryl diisocyanates contain 5 to 24 carbon atoms, and particularly preferred aryl diisocyanates contain 5 to 14 carbon atoms.
  • Exemplary aryl diisocyanates contain one aromatic ring or two fused or linked aromatic rings, e.g., phenyl, tolyl, xylyl, naphthyl, biphenyl, diphenylether, benzophenone, and the like.
  • Preferred aromatic diisocyanates include toluene diisocyanates, tetramethylxylene diisocyanate (TMXDI), and methylene diphenyl diisocyanate (MDI), which may comprise any mixture of its three isomers, 2.2'-MDI, 2,4'-MDI, and 4,4' -MDI.
  • Adhesion promoters that may be used in the present invention may be a polymer-containing isocyanate, such as, for example, diisocyanates.
  • Polymer-containing isocyanates refers to a polymer- containing two or more terminal and/or pendant alkyl or aryl isocyanate groups.
  • the polymer-containing isocyanates generally have to have a minimal solubility in the resin to provide improved mechanical properties.
  • Preferred polymer-containing isocyanates include, but are not limited to, PM200 (poly MDI), Lupranate ® (poly MDI from BASF), Krasol ® isocyanate terminated polybutadiene prepolymers, such as, for example, Krasol ® LBD2000 (TDI based), Krasol ® LBD3000 (TDI based), Krasol ® N -22 (MDI based), Krasol ® NN-23 (MDI based), Krasol ® N -25 (MDI based), and the like.
  • Krasol ® isocyanate terminated polybutadiene prepolymers are available from Cray Valley.
  • Adhesion promoters that may be used in the present invention may be a trimer of alkyl diisocyanates and aryl diisocyanates.
  • any combination of polyisocyanate compounds may be trimerized to form an isocyanurate ring containing isocyanate functional groups.
  • Trimers of alkyl diisocyanate and aryl diisocyanates may also be referred to as isocyanurates of alkyl diisocyanate or aryl diisocyanate.
  • Preferred alkyl diisocyanate and aryl diisocyanate trimers include, but are not limited to, hexamethylene diisocyanate trimer (HDIt), isophorone diisocyanate trimer, toluene diisocyanate trimer, tetramethylxylene diisocyanate trimer, methylene diphenyl diisocyanate trimers, and the like.
  • HDIt hexamethylene diisocyanate trimer
  • isophorone diisocyanate trimer isophorone diisocyanate trimer
  • toluene diisocyanate trimer toluene diisocyanate trimer
  • tetramethylxylene diisocyanate trimer methylene diphenyl diisocyanate trimers
  • More preferred adhesion promoters are toluene diisocyanates, tetramethylxylene diisocyanate (TMXDI), and methylene diphenyl diisocyanate (MDI) including any mixture of its three isomers 2.2' -MDI, 2,4' -MDI and 4,4' -MDI; liquid MDI; solid MDI; hexamethylenediisocyanatetrimer (HDIt);
  • HDI hexamethylenediisocyanate
  • IPDI isophorone diisocyanate
  • H12MDI 4,4 '-methylene bis(cyclohexyl isocyanate)
  • PM200 polymeric MDI
  • MDI prepolymer Liupranate ® 5080
  • liquid carbodiimide modified 4,4'-MDI Liupranate ® MM103
  • liquid MDI Liupranate ® MI
  • MDI Mondur ® ML
  • MDI Mondur ® MLQ
  • MDI methylene diphenyl diisocyanate
  • any mixture of its three isomers 2,2' -MDI, 2,4' -MDI and 4,4' -MDI liquid MDI; solid MDI; hexamethylenediisocyanatetrimer (HDIt); hexamethylene diisocyanate (HDI); isophorone diisocyanate (IPDI); 4,4 '-methylene bis(cyclohexyl isocyanate)
  • any concentration of adhesion promoter which improves the mechanical properties of the olefin composite is sufficient for the invention.
  • suitable amounts of adhesion promoter range from 0.001-50 phr, particularly 0.05-10 phr, more particularly 0.1- 10 phr, or even more particularly 0.5-4.0 phr.
  • One or more adhesion promoters may be used in the present invention.
  • Additional adhesion promoters suitable for use in the present invention comprise
  • Y* is selected from halide (preferably chloride) or OR
  • Fn is a functional group selected from acrylate, methacrylate, allyl, vinyl, alkene, cycloalkene, or norbornene
  • A is a divalent linking group selected from hydrocarbylene, substituted hydrocarbylene, heteroatom-containing hydrocarbylene, or substituted heteroatom-containing hydrocarbylene
  • n is 0 or 1
  • R is selected from hydrocarbyl, substituted hydrocarbyl, heteroatom- containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl, preferably lower alkyl, more preferably methyl, ethyl, or isopropyl
  • a peroxide selected from dialkyl and diaryl peroxides.
  • adhesion promoters for use in the present invention and methods for their use include those disclosed in International Pat. App. No. PCT/USOO/03002, the contents of which are incorporated herein by reference.
  • Resin compositions and/or cyclic olefin compositions that may be used with the present invention disclosed herein comprise one or more cyclic olefins.
  • any cyclic olefin suitable for the metathesis reactions disclosed herein may be used.
  • Such cyclic olefins may be optionally substituted, optionally heteroatom-containing, mono-unsaturated, di-unsaturated, or poly -unsaturated C5 to C24 hydrocarbons that may be mono-, di-, or poly-cyclic.
  • the cyclic olefin may generally be any strained or unstrained cyclic olefin, provided the cyclic olefin is able to participate in a ROMP reaction either individually or as part of a ROMP cyclic olefin composition or as part of a resin composition. While certain unstrained cyclic olefins such as cyclohexene are generally understood to not undergo ROMP reactions by themselves, under appropriate circumstances, such unstrained cyclic olefins may nonetheless be ROMP active. For example, when present as a co-monomer in a ROMP composition, unstrained cyclic olefins may be ROMP active.
  • unstrained cyclic olefin is intended to refer to those unstrained cyclic olefins that may undergo a ROMP reaction under any conditions, or in any ROMP composition, provided the unstrained cyclic olefin is ROMP active.
  • the cyclic olefin may be represented by the structure of formula (A)
  • R A1 and R A2 is selected independently from the group consisting of hydrogen, hydrocarbyl (e.g., C1-C20 alkyl, C5-C20 aryl, C5-C30 aralkyl, or C5-C30 alkaryl), substituted hydrocarbyl (e.g., substituted Ci- C2o alkyl, C5-C20 aryl, C5-C30 aralkyl, or C5-C30 alkaryl), heteroatom-containing hydrocarbyl (e.g., C1-C20 heteroalkyl, C5-C20 heteroaryl, heteroatom-containing C5-C30 aralkyl, or heteroatom-containing C5-C30 alkaryl), and substituted heteroatom-containing hydrocarbyl (e.g., substituted C1-C20 heteroalkyl, C5-C20 heteroaryl, heteroatom-containing C5-C30 aralkyl, or heteroatom-containing C5-C30 alkaryl) and, if substitute
  • R A1 and R A2 may itself be one of the aforementioned groups, such that the Fn moiety is directly bound to the olefinic carbon atom indicated in the structure.
  • the functional group will generally not be directly bound to the olefinic carbon through a heteroatom containing one or more lone pairs of electrons, e.g., an oxygen, sulfur, nitrogen, or phosphorus atom, or through an electron-rich metal or metalloid such as Ge, Sn, As, Sb, Se, Te, etc.
  • R A1 and/or R A2 there will normally be an intervening linkage Z * , such that R A1 and/or R A2 then has the structure -(Z * ) n -Fn wherein n is 1 , Fn is the functional group, and Z * is a hydrocarbylene linking group such as an alkylene, substituted alkylene, heteroalkylene, substituted heteroalkene, arylene, substituted arylene, heteroarylene, or substituted heteroarylene linkage.
  • J is a saturated or unsaturated hydrocarbylene, substituted hydrocarbylene, heteroatom- containing hydrocarbylene, or substituted heteroatom-containing hydrocarbylene linkage, wherein when J is substituted hydrocarbylene or substituted heteroatom-containing hydrocarbylene, the substituents may include one or more -(Z ) n -Fn groups, wherein n is zero or 1 , and Fn and Z are as defined previously. Additionally, two or more substituents attached to ring carbon (or other) atoms within J may be linked to form a bicyclic or polycyclic olefin.
  • J will generally contain in the range of approximately 5 to 14 ring atoms, typically 5 to 8 ring atoms, for a monocyclic olefin, and, for bicyclic and polycyclic olefins, each ring will generally contain 4 to 8, typically 5 to 7, ring atoms.
  • Mono-unsaturated cyclic olefins encompassed by structure (A) may be represented by the structure (B)
  • b is an integer generally although not necessarily in the range of 1 to 10, typically 1 to 5,
  • R A1 and R A2 are as defined above for structure (A), and R B1 , R B2 , R B3 , R B4 , R B5 , and R B6 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom- containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl and -(Z * ) n -Fn where n, Z * and Fn are as defined previously, and wherein if any of the R B1 through R B6 moieties is substituted hydrocarbyl or substituted heteroatom-containing hydrocarbyl, the substituents may include one or more -(Z * ) n -Fn groups.
  • R B1 , R B2 , R B3 , R B4 , R B5 , and R B6 may be, for example, hydrogen, hydroxyl, C1-C20 alkyl, C5-C20 aryl, C1-C20 alkoxy, C5-C20 aryloxy, C2-C20 alkoxycarbonyl, C5-C20 aryloxycarbonyl, amino, amido, nitro, etc.
  • any of the R B1 , R B2 , R B3 , R B4 , R B5 , and R B6 moieties can be linked to any of the other R B1 , R B2 , R B3 , R B4 , R B5 , and R B6 moieties to provide a substituted or unsubstituted alicyclic group containing 4 to 30 ring carbon atoms or a substituted or unsubstituted aryl group containing 6 to 18 ring carbon atoms or combinations thereof and the linkage may include heteroatoms or functional groups, e.g., the linkage may include without limitation an ether, ester, thioether, amino, alkylamino, imino, or anhydride moiety.
  • the alicyclic group can be monocyclic, bicyclic, or polycyclic.
  • the cyclic group can contain monounsaturation or multiunsaturation, with monounsaturated cyclic groups being preferred.
  • the rings When substituted, the rings contain monosubstitution or multisubstitution wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn are as defined previously, and functional groups (Fn) provided above.
  • Examples of monounsaturated, monocyclic olefins encompassed by structure (B) include, without limitation, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, cycloundecene, cyclododecene, tricyclodecene, tetracyclodecene, octacyclodecene, and cycloeicosene, and substituted versions thereof such as 1 -methylcyclopentene, 1 -ethylcyclopentene,
  • Monocyclic diene reactants encompassed by structure (A) may be generally represented by the structure (C)
  • R A1 and R A2 are as defined above for structure (A)
  • R C1 , R C2 , R C3 , R C4 , R C5 , and R C6 are defined as for R B1 through R B6 .
  • R C3 and R C4 be non-hydrogen substituents, in which case the second olefinic moiety is tetrasubstituted.
  • Examples of monocyclic diene reactants include, without limitation, 1,3-cyclopentadiene, 1,3-cyclohexadiene, 1,4- cyclohexadiene, 5-ethyl-l,3-cyclohexadiene, 1,3-cycloheptadiene, cyclohexadiene, 1,5-cyclooctadiene, 1,3-cyclooctadiene, and substituted analogs thereof.
  • Triene reactants are analogous to the diene structure (C), and will generally contain at least one methylene linkage between any two olefinic segments.
  • Bicyclic and polycyclic olefins encompassed by structure (A) may be generally represented by the structure (D)
  • R A1 and R A2 are as defined above for structure (A), R , R , R D3 , and R D4 are as defined for R B1 through R B6 , e is an integer in the range of 1 to 8 (typically 2 to 4) f is generally 1 or 2;
  • any of the R D1 , R D2 , R D3 , and R m moieties can be linked to any of the other R D1 , R D2 , R D3 , and R D4 moieties to provide a substituted or unsubstituted alicyclic group containing 4 to 30 ring carbon atoms or a substituted or unsubstituted aryl group containing 6 to 18 ring carbon atoms or combinations thereof and the linkage may include heteroatoms or functional groups, e.g., the linkage may include without limitation an ether, ester, thioether, amino, alkylamino, imino, or anhydride moiety.
  • the cyclic group can be monocyclic, bicyclic, or polycyclic.
  • unsaturated the cyclic group can contain monounsaturation or multiunsaturation, with monounsaturated cyclic groups being preferred.
  • substituted the rings contain monosubstitution or multisubstitution wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom- containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1 , Z * and Fn are as defined previously, and functional groups (Fn) provided above.
  • Cyclic olefins encompassed by structure (D) are in the norbomene family.
  • norbomene means any compound that includes at least one norbomene or substituted norbomene moiety, including without limitation norbomene, substituted norbomene(s), norbomadiene, substituted norbomadiene(s), polycyclic norbomenes, and substituted polycyclic norbomene(s).
  • Norbomenes within this group may be generally represented by the structure (E)
  • R and R are as defined above for structure (A), T is as defined above for structure (D), R , R E2 , R E3 , R m , R E5 , R E6 , R E7 , and R E8 are as defined for R B1 through R B6 , and "a" represents a single bond or a double bond, f is generally 1 or 2, "g” is an integer from 0 to 5, and when "a" is a double bond one of R E5 , R E6 and one of R E7 , R E8 is not present.
  • any of the R , R , R , and R b " moieties can be linked to any of the other R , R E6 , R E7 , and R E8 moieties to provide a substituted or unsubstituted alicyclic group containing 4 to 30 ring carbon atoms or a substituted or unsubstituted aryl group containing 6 to 18 ring carbon atoms or combinations thereof and the linkage may include heteroatoms or functional groups, e.g., the linkage may include without limitation an ether, ester, thioether, amino, alkylamino, imino, or anhydride moiety.
  • the cyclic group can be monocyclic, bicyclic, or polycyclic.
  • the cyclic group can contain monounsaturation or multiunsaturation, with monounsaturated cyclic groups being preferred.
  • the rings When substituted, the rings contain monosubstitution or multisubstitution wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn are as defined previously, and functional groups (Fn) provided above.
  • More preferred cyclic olefins possessing at least one norbornene moiety have the structure F):
  • R , R , R , and R are as defined for R through R , and "a" represents a single bond or a double bond, “g” is an integer from 0 to 5, and when “a” is a double bond one of R F1 , R F2 and one of R F3 , R F4 is not present.
  • any of the R F1 , R F2 , R F3 , and R F4 moieties can be linked to any of the other R F1 , R F2 , R F3 , and R F4 moieties to provide a substituted or unsubstituted alicyclic group containing 4 to 30 ring carbon atoms or a substituted or unsubstituted aryl group containing 6 to 18 ring carbon atoms or combinations thereof and the linkage may include heteroatoms or functional groups, e.g., the linkage may include without limitation an ether, ester, thioether, amino, alkylamino, imino, or anhydride moiety.
  • the alicyclic group can be monocyclic, bicyclic, or polycyclic.
  • the cyclic group can contain monounsaturation or multiunsaturation, with monounsaturated cyclic groups being preferred.
  • the rings When substituted, the rings contain monosubstitution or multisubstitution wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z ) n -Fn where n is zero or 1, Z and Fn are as defined previously, and functional groups (Fn) provided above.
  • R F1 to R F4 are as previously defined for structure (F).
  • Norbornadiene and higher Diels-Alder adducts thereof similarly can be prepared by the thermal reaction of cyclopentadiene and dicyclopentadiene in the presence of an acetylenic reactant as shown below in Scheme 3 : wherein "g” is an integer from 0 to 5, R and R are as previously defined for structure (F)
  • bicyclic and polycyclic olefins thus include, without limitation,
  • DCPD dicyclopentadiene
  • trimer and other higher order oligomers of cyclopentadiene including without limitation tricyclopentadiene (cyclopentadiene trimer), cyclopentadiene tetramer, and cyclopentadiene pentamer; ethylidenenorbornene; dicyclohexadiene; norbornene; 5-methyl-2-norbornene; 5-ethyl-2- norbornene; 5-isobutyl-2-norbornene; 5,6-dimethyl-2-norbornene; 5-phenylnorbornene; 5- benzylnorbornene; 5-acetylnorbornene; 5-methoxycarbonylnorbornene; 5-ethyoxycarbonyl-l -norbornene; 5-methyl-5-methoxy-carbonylnorbornene; 5-cyanonorbornene; 5,5,6-trimethyl-2-norbornene;
  • bicyclic and polycyclic olefins include, without limitation, C2-C12 hydrocarbyl substituted norbornenes such as 5-butyl-2-norbornene, 5-hexyl-2-norbornene, 5-octyl-2-norbornene, 5-decyl-2-norbornene, 5- dodecyl-2-norbornene, 5-vinyl-2-norbornene, 5-ethylidene-2-norbornene, 5-isopropenyl-2-norbornene, 5- propenyl-2-norbornene, and 5-butenyl-2-norbornene, and the like.
  • C2-C12 hydrocarbyl substituted norbornenes such as 5-butyl-2-norbornene, 5-hexyl-2-norbornene, 5-octyl-2-norbornene, 5-decyl-2-norbornene, 5- dodecyl-2-norbornene
  • bicyclic and polycyclic olefins as disclosed herein may consist of a variety of structural isomers and/or stereoisomers, any and all of which are suitable for use in the present invention. Any reference herein to such bicyclic and polycyclic olefins unless specifically stated includes mixtures of any and all such structural isomers and/or stereoisomers.
  • Preferred cyclic olefins include C5 to C24 unsaturated hydrocarbons. Also preferred are C5 to C24 cyclic hydrocarbons that contain one or more (typically 2 to 12) heteroatoms such as O, N, S, or P. For example, crown ether cyclic olefins may include numerous O heteroatoms throughout the cycle, and these are within the scope of the invention. In addition, preferred cyclic olefins are C5 to C24
  • hydrocarbons that contain one or more (typically 2 or 3) olefins.
  • the cyclic olefin may be mono-, di-, or tri-unsaturated.
  • examples of cyclic olefins include without limitation cyclooctene, cyclododecene, and (c,t,t)-l,5,9-cyclododecatriene.
  • the cyclic olefins may also comprise multiple (typically 2 or 3) rings.
  • the cyclic olefin may be mono-, di-, or tri-cyclic.
  • the rings may or may not be fused.
  • Preferred examples of cyclic olefins that comprise multiple rings include norbornene, dicyclopentadiene, tricyclopentadiene, and 5-ethylidene-2-norbornene.
  • the cyclic olefin may also be substituted, for example, a C5 to C24 cyclic hydrocarbon wherein one or more (typically 2, 3, 4, or 5) of the hydrogens are replaced with non-hydrogen substituents.
  • Suitable non-hydrogen substituents may be chosen from the substituents described hereinabove.
  • functionalized cyclic olefins i.e., C5 to C24 cyclic hydrocarbons wherein one or more (typically 2, 3, 4, or 5) of the hydrogens are replaced with functional groups, are within the scope of the invention.
  • Suitable functional groups may be chosen from the functional groups described hereinabove.
  • a cyclic olefin functionalized with an alcohol group may be used to prepare a telechelic polymer comprising pendent alcohol groups.
  • Functional groups on the cyclic olefin may be protected in cases where the functional group interferes with the metathesis catalyst, and any of the protecting groups commonly used in the art may be employed. Acceptable protecting groups may be found, for example, in Greene et al., Protective Groups in Organic Synthesis, 3rd Ed. (New York: Wiley, 1999).
  • Examples of functionalized cyclic olefins include without limitation 2-hydroxymethyl-5- norbornene, 2-[(2-hydroxyethyl)carboxylate]-5-norbornene, cydecanol, 5-n-hexyl-2-norbornene, 5-n- butyl-2-norbornene.
  • Cyclic olefins incorporating any combination of the abovementioned features are suitable for the methods disclosed herein. Additionally, cyclic olefins incorporating any combination of the abovementioned features (i.e., heteroatoms, substituents, multiple olefins, multiple rings) are suitable for the invention disclosed herein.
  • the cyclic olefins useful in the methods disclosed herein may be strained or unstrained. It will be appreciated that the amount of ring strain varies for each cyclic olefin compound, and depends upon a number of factors including the size of the ring, the presence and identity of substituents, and the presence of multiple rings. Ring strain is one factor in determining the reactivity of a molecule towards ring-opening olefin metathesis reactions. Highly strained cyclic olefins, such as certain bicyclic compounds, readily undergo ring opening reactions with olefin metathesis catalysts.
  • strained cyclic olefins such as certain unsubstituted hydrocarbon monocyclic olefins
  • ring opening reactions of relatively unstrained (and therefore relatively unreactive) cyclic olefins may become possible when performed in the presence of the olefinic compounds disclosed herein.
  • cyclic olefins useful in the invention disclosed herein may be strained or unstrained.
  • the resin compositions and/or cyclic olefin compositions of the present invention may comprise a plurality of cyclic olefins.
  • a plurality of cyclic olefins may be used to prepare metathesis polymers from the olefinic compound.
  • two cyclic olefins selected from the cyclic olefins described hereinabove may be employed in order to form metathesis products that incorporate both cyclic olefins.
  • a second cyclic olefin is a cyclic alkenol, i.e., a C5-C24 cyclic hydrocarbon wherein at least one of the hydrogen substituents is replaced with an alcohol or protected alcohol moiety to yield a functionalized cyclic olefin.
  • a plurality of cyclic olefins allows for further control over the positioning of functional groups within the products.
  • the density of cross-linking points can be controlled in polymers and macromonomers prepared using the methods disclosed herein.
  • Control over the quantity and density of substituents and functional groups also allows for control over the physical properties (e.g., melting point, tensile strength, glass transition temperature, etc.) of the products. Control over these and other properties is possible for reactions using only a single cyclic olefin, but it will be appreciated that the use of a plurality of cyclic olefins further enhances the range of possible metathesis products and polymers formed.
  • More preferred cyclic olefins include dicyclopentadiene; tricyclopentadiene;
  • cyclopentadiene tricyclopentadiene, and higher order oligomers of cyclopentadiene, such as cyclopentadiene tetramer, cyclopentadiene pentamer, and the like, tetracyclododecene, norbomene, and C2-C12 hydrocarbyl substituted norbomenes, such as 5-butyl-2-norbornene, 5-hexyl-2-norbornene, 5-octyl-2-norbornene, 5- decyl-2-norbornene, 5-dodecyl-2-norbomene, 5-vinyl-2-norbomene, 5-ethylidene-2-norbomene, 5- isopropenyl-2-norbomene, 5-propenyl-2-norbornene, 5-butenyl-2-norbomene, and the like.
  • Cyclic olefins include dicyclopentadiene, tricyclopentadiene, and higher order oligomers of cyclopentadiene, such as cyclopentadiene tetramer, cyclopentadiene pentamer, and the like, 5-tolyl-2- norbomene, 5-phenyl-2-norbornene, C2-C12 hydrocarbyl substituted norbomenes, such as 5-hexyl-2- norbomene, 5-octyl-2-norbornene, 5-decyl-2-norbornene, 5-dodecyl-2-norbornene , and the like.
  • Cyclic olefins that contain multiunsaturation include dicyclopentadiene, tricyclopentadiene, and higher order oligomers of cyclopentadiene, such as cyclopentadiene tetramer, cyclopentadiene pentamer, and the like, and 5-vinyl-2-norbornene, 5-ethylidene-2-norbornene, 5-isopropenyl-2- norbomene, 5-propenyl-2-norbornene, 5-butenyl-2-norbornene, and the like.
  • Cyclic olefins that contain multiunsaturation include dicyclopentadiene, tricyclopentadiene, and higher order oligomers of cyclopentadiene, such as cyclopentadiene tetramer, cyclopentadiene pentamer, and the like.
  • Cyclic olefins that contain multiunsaturation include dicyclopentadiene, tricyclopentadiene, and higher order oligomers of cyclopentadiene, such as cyclopentadiene tetramer.
  • Cyclic olefins that contain multiunsaturation include dicyclopentadiene, tricyclopentadiene, and tetracyclopentadiene.
  • An example of a cyclic olefin that contains multiunsaturation is dicyclopentadiene.
  • An example of a cyclic olefin that contains multiunsaturation is tricyclopentadiene.
  • An example of a cyclic olefin that contains multiunsaturation is tetracyclopentadiene.
  • Cyclic olefins that contain monounsaturation include 5-tolyl-2-norbornene, 5-phenyl-2- norbomene, 5-butyl-2-norbornene, 5-hexyl-2-norbornene, 5-octyl-2-norbornene, 5-decyl-2-norbornene, 5- dodecyl-2-norbornene.
  • Cyclic olefins that contain monounsaturation include 5-tolyl-2-norbornene, 5-phenyl-2- norbomene.
  • Cyclic olefins that contain monounsaturation include 5-butyl-2-norbornene, 5-hexyl-2- norbomene, 5-octyl-2-norbornene, 5-decyl-2-norbornene, 5-dodecyl-2-norbornene [000415] Cyclic olefins that contain monounsaturation include 5-hexyl-2-norbornene, 5-octyl-2- norbornene, 5-decyl-2-norbornene.
  • Cyclic olefins that contain monounsaturation include 5-hexyl-2-norbornene, 5-octyl-2- norbornene, 5-decyl-2-norbornene, and 5-tolyl-2-norbornene.
  • Cyclic olefins that contain monounsaturation include 5-hexyl-2-norbornene, 5-octyl-2- norbornene, 5-decyl-2-norbornene, 5-tolyl-2-norbornene, and 5-phenyl-2-norbornene.
  • Cyclic olefins that contain monounsaturation include 5-octyl-2-norbornene and 5-decyl-2- norbornene.
  • Cyclic olefins that contain monounsaturation include C2-C12 hydrocarbyl substituted norbornenes.
  • Cyclic olefins that contain monomunsaturation include C4-C12 hydrocarbyl substituted norbornenes.
  • Cyclic olefins that contain monounsaturation include C6-C12 hydrocarbyl substituted norbornenes.
  • Cyclic olefins that contain monomunsaturation include C6-C10 hydrocarbyl substituted norbornenes.
  • An example of a cyclic olefin that contains monounsaturation is 5-octyl-2-norbornene.
  • An example of a cyclic olefin that contains monounsaturation is 5-decyl-2-norbornene.
  • An example of a cyclic olefin that contains monounsaturation is 5-hexyl-2-norbornene.
  • An example of a cyclic olefin that contains monounsaturation is 5-phenyl-2-norbornene.
  • An example of a cyclic olefin that contains monounsaturation is 5-tolyl-2-norbornene.
  • An example of a cyclic olefin that contains monounsaturation is 5-butyl-2-norbornene.
  • An example of a cyclic olefin that contains monounsaturation is 5-dodecyl-2-norbornene.
  • the cyclic olefin compositions of the invention and for use in the invention comprise at least one cyclic olefin containing multiunsaturation and at least one cyclic olefin containing monounsaturation, where the amount of at least one cyclic olefin containing multiunsaturation may be present in an amount that ranges from 10.0 mol% to 80.0 mol%, 10.0 mol% to 70.0 mol%, 10.0 mol% to 60.0 mol%, 10.0 mol% to 50.0 mol%, 10.0 mol% to 40.0 mol%, 10.0 mol% to 30.0 mol%, 10.0 mol% to 20.0 mol%, 20.0 mol% to 80.0 mol%, 20.0 mol% to 70.0 mol%, 20.0 mol% to 60.0 mol%, 20.0 mol% to 50.0 mol%, 20.0 mol% to 40.0 mol%, 20.0 mol% to 30.0 mol%
  • the cyclic olefin compositions of the invention and for use in the invention comprise at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom- containing hydrocarbyl, substituted heteroatom-containing
  • multiunsaturation may be present in an amount that ranges from 10.0 mol% to 80.0 mol%, 10.0 mol% to 70.0 mol%, 10.0 mol% to 60.0 mol%, 10.0 mol% to 50.0 mol%, 10.0 mol% to 40.0 mol%, 10.0 mol% to 30.0 mol%, 10.0 mol% to 20.0 mol%, 20.0 mol% to 80.0 mol%, 20.0 mol% to 70.0 mol%, 20.0 mol% to 60.0 mol%, 20.0 mol% to 50.0 mol%, 20.0 mol% to 40.0 mol%, 20.0 mol% to 30.0 mol%, 30.0 mol% to 80.0 mol%, 30.0 mol% to 70.0 mol%, 30.0 mol% to 60.0 mol%, 30.0 mol% to 50.0 mol%, 30.0 mol% to 40.0 mol%, 40.0 mol% to 80.0 mol%, 40.0 mol% to 70.0 mol%
  • the cyclic olefin compositions of the invention and for use in the invention comprise at least one cyclic olefin containing multiunsaturation and at least one cyclic olefin containing monounsaturation, where the amount of at least one cyclic olefin containing multiunsaturation may be present in an amount that ranges from 10.0 mol% to 80.0 mol%, 10.0 mol% to 70.0 mol%, 10.0 mol% to 60.0 mol%, 10.0 mol% to 50.0 mol%, 10.0 mol% to 40.0 mol%, 10.0 mol% to 30.0 mol%, 10.0 mol% to 20.0 mol%, 20.0 mol% to 80.0 mol%, 20.0 mol% to 70.0 mol%, 20.0 mol% to 60.0 mol%, 20.0 mol% to 50.0 mol%, 20.0 mol% to 40.0 mol%, 20.0 mol% to 30.0 mol%, 10.0 mol% to 2
  • the cyclic olefin compositions of the invention and for use in the invention comprise at least one cyclic olefin containing multiunsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, -(Z * ) n -Fn where n is zero or 1, Z * and Fn, and functional groups (Fn); and at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom- containing hydrocarbyl, substituted heteroatom-containing
  • multiunsaturation may be present in an amount that ranges from 10.0 mol% to 80.0 mol%, 10.0 mol% to 70.0 mol%, 10.0 mol% to 60.0 mol%, 10.0 mol% to 50.0 mol%, 10.0 mol% to 40.0 mol%, 10.0 mol% to 30.0 mol%, 10.0 mol% to 20.0 mol%, 20.0 mol% to 80.0 mol%, 20.0 mol% to 70.0 mol%, 20.0 mol% to 60.0 mol%, 20.0 mol% to 50.0 mol%, 20.0 mol% to 40.0 mol%, 20.0 mol% to 30.0 mol%, 30.0 mol% to 80.0 mol%, 30.0 mol% to 70.0 mol%, 30.0 mol% to 60.0 mol%, 30.0 mol% to 50.0 mol%, 30.0 mol% to 40.0 mol%, 40.0 mol% to 80.0 mol%, 40.0 mol% to 70.0 mol%
  • a metal carbene olefin metathesis catalyst that may be used in the invention disclosed herein, is preferably a Group 8 transition metal complex having the structure of formula (I)
  • M is a Group 8 transition metal
  • L 1 , L 2 , and L 3 are neutral electron donor ligands
  • n 0 or 1 , such that L 3 may or may not be present;
  • n 0, 1, or 2;
  • k is 0 or 1 ;
  • X 1 and X 2 are anionic ligands
  • R 1 and R 2 are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups,
  • any two or more of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 can be taken together to form one or more cyclic groups, and further wherein any one or more of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 may be attached to a support.
  • R 1 and R 2 may have the structure -(W ⁇ -U ⁇ V " , in which W is selected from hydrocarbylene, substituted hydrocarbylene, heteroatom-containing hydrocarbylene, or substituted heteroatom-containing hydrocarbylene; U is a positively charged Group 15 or Group 16 element substituted with hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom- containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl; V is a negatively charged counterion; and n is zero or 1. Furthermore, R 1 and R 2 may be taken together to form an indenylidene moiety.
  • Preferred catalysts contain Ru or Os as the Group 8 transition metal, with Ru particularly preferred.
  • a first group of catalysts are commonly referred to as First Generation Grubbs-type catalysts, and have the structure of formula (I).
  • M is a Group 8 transition metal
  • m is 0, 1, or 2
  • n X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 are described as follows.
  • n is 0, and L 1 and L 2 are independently selected from phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibine, ether, (including cyclic ethers), amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, substituted pyridine, imidazole, substituted imidazole, pyrazine, substituted pyrazine and thioether.
  • Exemplary ligands are trisubstituted phosphines.
  • Preferred trisubstituted phosphines are of the formula PR H1 R H2 R H3 , where R H1 , R m , and R m are each independently substituted or unsubstituted aryl or Ci-Cio alkyl, particularly primary alkyl, secondary alkyl, or cycloalkyl.
  • L 1 and L 2 are independently selected from the group consisting of trimethylphosphine (PMe3), triethylphosphine (PEt3), tri-n-butylphosphine ( ⁇ 3 ⁇ 4), tri(ortho-tolyl)phosphine (P-o-tolyb), tri-tert-butylphosphine (P-tert-Bu3), tricyclopentylphosphine (PCyclopentyb), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), trioctylphosphine (POct3), triisobutylphosphine, ( ⁇ - ⁇ - ⁇ 3 ⁇ 4), triphenylphosphine (PPI13), tri(pentafluorophenyl)phosphine (P(C6F5)3), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenyl
  • L 1 and L 2 may be independently selected from phosphabicycloalkane (e.g., monosubstituted 9-phosphabicyclo-[3.3.1]nonane, or monosubstituted 9- phosphabicyclo[4.2.1]nonane] such as cyclohexylphoban, isopropylphoban, ethylphoban, methylphoban, butylphoban, pentylphoban and the like).
  • phosphabicycloalkane e.g., monosubstituted 9-phosphabicyclo-[3.3.1]nonane, or monosubstituted 9- phosphabicyclo[4.2.1]nonane
  • cyclohexylphoban isopropylphoban
  • ethylphoban methylphoban
  • butylphoban pentylphoban and the like
  • X 1 and X 2 are anionic ligands, and may be the same or different, or are linked together to form a cyclic group, typically although not necessarily a five- to eight-membered ring.
  • X 1 and X 2 may be substituted with one or more moieties selected from C1-C12 alkyl, C1-C12 alkoxy, C5-C24 aryl, and halide, which may, in turn, with the exception of halide, be further substituted with one or more groups selected from halide, Ci-Ce alkyl, Ci-Ce alkoxy, and phenyl.
  • X 1 and X 2 are halide, benzoate, d-Ce acyl, d-Ce alkoxycarbonyl, Ci-Ce alkyl, phenoxy, Ci-Ce alkoxy, Ci-Ce alkylsulfanyl, aryl, or Ci-Ce alkylsulfonyl.
  • X 1 and X 2 are each halide, CF3CO2, CH3CO2, CFH2CO2, (CH 3 ) 3 CO, (CF 3 ) 2 (CH 3 )CO, (CF 3 )(CH 3 ) 2 CO, PhO, MeO, EtO, tosylate, mesylate, or trifluoromethane-sulfonate.
  • X 1 and X 2 are each chloride.
  • R 1 and R 2 are independently selected from hydrogen, hydrocarbyl (e.g., C 1 -C 2 0 alkyl, C 2 -C 2 0 alkenyl, C2-C20 alkynyl, C5-C24 aryl, C6-C24 alkaryl, C6-C24 aralkyl, etc.), substituted hydrocarbyl (e.g., substituted C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C5-C24 aryl, C6-C24 alkaryl, C6-C24 aralkyl, etc.), heteroatom-containing hydrocarbyl (e.g., heteroatom-containing C 1 -C 2 0 alkyl, C 2 -C 2 0 alkenyl, C 2 -C 2 0 alkynyl, C5-C24 aryl, C6-C24 alkaryl, C6-C24 aralkyl, etc.
  • R 1 and R 2 may also be linked to form a cyclic group, which may be aliphatic or aromatic, and may contain substituents and/or heteroatoms. Generally, such a cyclic group will contain 4 to 12, preferably 5, 6, 7, or 8 ring atoms.
  • R 1 is hydrogen and R 2 is selected from C1-C20 alkyl, C2-C20 alkenyl, and C5-C24 aryl, more preferably Ci-Ce alkyl, d-Ce alkenyl, and C5-C14 aryl. Still more preferably, R 2 is phenyl, vinyl, methyl, isopropyl, or t-butyl, optionally substituted with one or more moieties selected from Ci-Ce alkyl, Ci-Ce alkoxy, phenyl, and a functional group Fn as defined earlier herein.
  • R 2 is phenyl or vinyl substituted with one or more moieties selected from methyl, ethyl, chloro, bromo, iodo, fluoro, nitro, dimethylamino, methyl, methoxy, and phenyl.
  • Any two or more (typically two, three, or four) of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 can be taken together to form a cyclic group, including bidentate or multidentate ligands, as disclosed, for example, in U.S. Patent No. 5,312,940, the disclosure of which is incorporated herein by reference.
  • X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 are linked to form cyclic groups
  • those cyclic groups may contain 4 to 12, preferably 4, 5, 6, 7 or 8 atoms, or may comprise two or three of such rings, which may be either fused or linked.
  • the cyclic groups may be aliphatic or aromatic, and may be heteroatom-containing and/or substituted.
  • the cyclic group may, in some cases, form a bidentate ligand or a tridentate ligand.
  • bidentate ligands include, but are not limited to, bisphosphines, dialkoxides,
  • alkyldiketonates alkyldiketonates, and aryldiketonates.
  • a second group of catalysts commonly referred to as Second Generation Grubbs-type catalysts, have the structure of formula (I), wherein L 1 is a carbene ligand having the structure of formula (II)
  • X and Y are heteroatoms typically selected from N, O, S, and P. Since O and S are divalent, p is necessarily zero when X is O or S, q is necessarily zero when Y is O or S, and k is zero or 1. However, when X is N or P, then p is 1 , and when Y is N or P, then q is 1. In a preferred embodiment, both X and Y are N;
  • Q 1 , Q 2 , Q 3 , and Q 4 are linkers, e.g., hydrocarbylene (including substituted hydrocarbylene, heteroatom-containing hydrocarbylene, and substituted heteroatom-containing hydrocarbylene, such as substituted and/or heteroatom-containing alkylene) or -(CO)-, and w, x, y, and z are independently zero or 1, meaning that each linker is optional. Preferably, w, x, y, and z are all zero. Further, two or more substituents on adjacent atoms within Q 1 , Q 2 , Q 3 , and Q 4 may be linked to form an additional cyclic group; and
  • R , R , R , and R are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl.
  • X and Y may be independently selected from carbon and one of the heteroatoms mentioned above, preferably no more than one of X or Y is carbon.
  • L 2 and L 3 may be taken together to form a single bindentate electron-donating heterocyclic ligand.
  • R 1 and R 2 may be taken together to form an indenylidene moiety.
  • X 1 , X 2 , L 2 , L 3 , X and Y may be further coordinated to boron or to a carboxylate.
  • any two or more of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , R 2 , R 3 , R 3A , R 4 , R 4A , Q 1 , Q 2 , Q 3 , and Q 4 can be taken together to form a cyclic group, and any one or more of X 1 , X 2 , L 2 , L 3 , Q 1 , Q 2 , Q 3 , Q 4 , R 1 , R 2 , R 3 , R 3A , R 4 , and R 4A may be attached to a support.
  • any two or more of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , R 2 , R 3 , R 3A , R 4 , and R 4A can also be taken to be -A-Fn, wherein "A" is a divalent hydrocarbon moiety selected from alkylene and arylalkylene, wherein the alkyl portion of the alkylene and arylalkylene groups can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, wherein the aryl portion of the of arylalkylene can be substituted or unsubstituted, and wherein hetero atoms and/or functional groups may be present in either the aryl or the alkyl portions of the alkylene and arylalkylene groups, and Fn is a functional group, or together to form a cyclic group, and any one or more of X 1 , X 2 , L 2
  • a particular class of carbene ligands having the structure of formula (II), where R 3A and R 4A are linked to form a cyclic group and at least one of X or Y is a nitrogen, or at least one of Q 3 or Q 4 is a heteroatom-containing hydrocarbylene or substituted heteroatom-containing hydrocarbylene, where at least one heteroatom is a nitrogen, are commonly referred to as N-heterocyclic carbene (NHC) ligands.
  • N-heterocyclic carbene (NHC) ligands are commonly referred to as N-heterocyclic carbene (NHC) ligands.
  • R 3A and R 4A are linked to form a cyclic group so that the carbene ligand has the structure of formula (IV)
  • R and R are as defined for the second group of catalysts above, with preferably at least one of R 3 and R 4 , and more preferably both R 3 and R 4 , being alicyclic or aromatic of one to about five rings, and optionally containing one or more heteroatoms and/or substituents.
  • Q is a linker, typically a hydrocarbylene linker, including substituted hydrocarbylene, heteroatom-containing hydrocarbylene, and substituted heteroatom-containing hydrocarbylene linkers, wherein two or more substituents on adjacent atoms within Q may also be linked to form an additional cyclic structure, which may be similarly substituted to provide a fused polycyclic structure of two to about five cyclic groups.
  • Q is often, although not necessarily, a two-atom linkage or a three-atom linkage.
  • N-heterocyclic carbene (NHC) ligands and acyclic diaminocarbene ligands suitable as L 1 thus include, but are not limited to, the following where DIPP or DiPP is diisopropylphenyl and Mes is 2,4,6-trimethylphenyl:
  • N-heterocyclic carbene (NHC) ligands and acyclic diaminocarbene ligands suitable as L 1 thus include, but are not limited to the following:
  • R , R , R , R are independently hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, or heteroatom containing hydrocarbyl, and where one or both of R w3 and R w4 may be in independently selected from halogen, nitro, amido, carboxyl, alkoxy, aryloxy, sulfonyl, carbonyl, thio, or nitroso groups.
  • N-heterocyclic carbene (NHC) ligands suitable as L 1 are further described in U.S. Pat. Nos. 7,378,528; 7,652, 145; 7,294,717; 6,787,620; 6,635,768; and 6,552,139, the contents of each are incorporated herein by reference.
  • thermally activated N-Heterocyclic Carbene Precursors as disclosed in U.S. Pat. No. 6,838,489, the contents of which are incorporated herein by reference, may also be used with the present invention.
  • Examples of functional groups here include without limitation carboxyl, C1-C20 alkoxy, C5-C24 aryloxy, C2-C20 alkoxycarbonyl, C5-C24 alkoxycarbonyl, C2-C24 acyloxy, C1-C20 alkylthio, C5-C24 arylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, optionally substituted with one or more moieties selected from C1-C12 alkyl, C1-C12 alkoxy, C5-C14 aryl, hydroxyl, sulfhydryl, formyl, and halide.
  • R 11 , R 12 , R 13 , and R 14 are preferably independently selected from hydrogen, C1-C12 alkyl, substituted C1-C12 alkyl, C1-C12 heteroalkyl, substituted C1-C12 heteroalkyl, phenyl, and substituted phenyl.
  • any two of R 11 , R 12 , R 13 , and R 14 may be linked together to form a substituted or unsubstituted, saturated or unsaturated ring structure, e.g., a C4- C 12 alicyclic group or a C5 or aryl group, which may itself be substituted, e.g., with linked or fused alicyclic or aromatic groups, or with other substituents.
  • any one or more of R 11 , R 12 , R 13 , and R 14 comprises one or more of the linkers.
  • R 3 and R 4 may be unsubstituted phenyl or phenyl substituted with one or more substituents selected from C 1 -C 2 0 alkyl, substituted C 1 -C 2 0 alkyl, C1-C20 heteroalkyl, substituted C1-C20 heteroalkyl, C5-C24 aryl, substituted C5-C24 aryl, C5-C24 heteroaryl, C6-C24 aralkyl, C6-C24 alkaryl, or halide.
  • X 1 and X 2 may be halogen.
  • R 3 and R 4 are aromatic, they are typically although not necessarily composed of one or two aromatic rings, which may or may not be substituted, e.g., R 3 and R 4 may be phenyl, substituted phenyl, biphenyl, substituted biphenyl, or the like.
  • R 3 and R 4 are the same and are each unsubstituted phenyl or phenyl substituted with up to three substituents selected from C1-C20 alkyl, substituted C1-C20 alkyl, C1-C20 heteroalkyl, substituted C1-C20 heteroalkyl, C5-C24 aryl, substituted C5-C24 aryl, C5-C24 heteroaryl, C6-C24 aralkyl, C6-C24 alkaryl, or halide.
  • any substituents present are hydrogen, C1-C12 alkyl, C1-C12 alkoxy, C5-C14 aryl, substituted C5-C14 aryl, or halide.
  • R 3 and R 4 are mesityl (i.e., Mes as defined herein).
  • M, m, n, X 1 , X 2 , R 1 , and R 2 are as defined for the first group of catalysts, L 1 is a strongly coordinating neutral electron donor ligand such as any of those described for the first and second group of catalysts, and L 2 and L 3 are weakly coordinating neutral electron donor ligands in the form of optionally substituted heterocyclic groups.
  • n is zero or 1 , such that L 3 may or may not be present.
  • L 2 and L 3 are optionally substituted five- or six-membered monocyclic groups containing 1 to 4, preferably 1 to 3, most preferably 1 to 2 heteroatoms, or are optionally substituted bicyclic or polycyclic structures composed of 2 to 5 such five- or six-membered monocyclic groups. If the heterocyclic group is substituted, it should not be substituted on a coordinating heteroatom, and any one cyclic moiety within a heterocyclic group will generally not be substituted with more than 3 substituents.
  • examples of L 2 and L 3 include, without limitation, heterocycles containing nitrogen, sulfur, oxygen, or a mixture thereof.
  • Examples of nitrogen-containing heterocycles appropriate for L 2 and L 3 include pyridine, bipyridine, pyridazine, pyrimidine, bipyridamine, pyrazine, 1,3,5-triazine, 1 ,2,4-triazine, 1,2,3-triazine, pyrrole, 2H -pyrrole, 3H-pyrrole, pyrazole, 2H-imidazole, 1,2,3-triazole, 1 ,2,4-triazole, indole, 3H-indole, lH-isoindole, cyclopenta(b)pyridine, indazole, quinoline, bisquinoline, isoquinoline, bisisoquinoline, cinnoline, quinazoline, naphthyridine, piperidine, piperazine, pyrrolidine, pyrazolidine, quinuclidine, imidazolidine, picolylimine, purine, benz
  • Examples of sulfur-containing heterocycles appropriate for L 2 and L 3 include thiophene, 1,2- dithiole, 1,3-dithiole, thiepin, benzo(b)thiophene, benzo(c)thiophene, thionaphthene, dibenzothiophene, 2H-thiopyran, 4H-thiopyran, and thioanthrene.
  • Examples of oxygen-containing heterocycles appropriate for L 2 and L 3 include 2H-pyran, 4H- pyran, 2-pyrone, 4-pyrone, 1,2-dioxin, 1,3-dioxin, oxepin, furan, 2H- 1 -benzopyran, coumarin, coumarone, chromene, chroman-4-one, isochromen- 1 -one, isochromen-3-one, xanthene, tetrahydrofuran, 1,4-dioxan, and dibenzofuran.
  • Examples of mixed heterocycles appropriate for L 2 and L 3 include isoxazole, oxazole, thiazole, isothiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,3,4-oxatriazole, 1,2,3,5- oxatriazole, 3H-l,2,3-dioxazole, 3H-l,2-oxathiole, 1,3-oxathiole, 4H- 1 ,2-oxazine, 2H- l,3-oxazine, 1,4- oxazine, 1,2,5-oxathiazine, o-isooxazine, phenoxazine, phenothiazine, pyrano[3,4-b]pyrrole, indoxazine, benzoxazole, anthranil, and morpholine.
  • L 2 and L 3 ligands are aromatic nitrogen-containing and oxygen-containing heterocycles, and particularly preferred L 2 and L 3 ligands are monocyclic N-heteroaryl ligands that are optionally substituted with 1 to 3, preferably 1 or 2, substituents.
  • L 2 and L 3 ligands are pyridine and substituted pyridines, such as 3-bromopyridine, 4- bromopyridine, 3,5-dibromopyridine, 2,4,6-tribromopyridine, 2,6-dibromopyridine, 3-chloropyridine, 4- chloropyridine, 3,5-dichloropyridine, 2,4,6-trichloropyridine, 2,6-dichloropyridine, 4-iodopyridine, 3,5- diiodopyridine, 3,5-dibromo-4-methylpyridine, 3,5-dichloro-4-methylpyridine, 3,5-dimethyl-4- bromopyridine, 3,5-dimethylpyridine, 4-methylpyridine, 3,5-diisopropylpyridine, 2,4,6-trimethylpyridine, 2,4,6-triisopropylpyridine, 4-(tert-butyl)pyridine, 4-phenylpyridine, 3,5-diphenylpyridine, 3,5-dichloro-4
  • any substituents present on L 2 and/or L 3 are selected from halo, C1-C20 alkyl, substituted C1-C20 alkyl, C1-C20 heteroalkyl, substituted C1-C20 heteroalkyl, Cs-C24 aryl, substituted C5-C24 aryl, C5-C24 heteroaryl, substituted C5-C24 heteroaryl, C6-C24 alkaryl, substituted C6-C24 alkaryl, C6-C24 heteroalkaryl, substituted C6-C24 heteroalkaryl, C6-C24 aralkyl, substituted C6-C24 aralkyl, C6-C24 heteroaralkyl, substituted C6-C 24 heteroaralkyl, and functional groups, with suitable functional groups including, without limitation, C 1 -C 2 0 alkoxy, C5-C 24 aryloxy, C 2 -C 2 0 alkylcarbonyl, C6-C 24
  • Preferred substituents on L 2 and L 3 include, without limitation, halo, C1-C12 alkyl, substituted C1-C12 alkyl, C1-C12 heteroalkyl, substituted C1-C12 heteroalkyl, Cs-Cw aryl, substituted Cs-Cw aryl, C5- Ci4 heteroaryl, substituted C5-C14 heteroaryl, C6-C16 alkaryl, substituted C6-C16 alkaryl, C6-C16 heteroalkaryl, substituted C6-C16 heteroalkaryl, C6-C16 aralkyl, substituted C6-C16 aralkyl, C6-C16 heteroaralkyl, substituted C6-C16 heteroaralkyl, C 1 -C 12 alkoxy, C5-C14 aryloxy, C 2 -C 12 alkylcarbonyl, Ce- Ci 4 arylcarbonyl, C 2 -C 12 alkylcarbonyloxy,
  • substituents are halo, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, phenyl, substituted phenyl, formyl, N,N-di(Ci-C6 alkyl)amino, nitro, and nitrogen heterocycles as described above (including, for example, pyrrolidine, piperidine, piperazine, pyrazine, pyrimidine, pyridine, pyridazine, etc.).
  • L 2 and L 3 may also be taken together to form a bidentate or multidentate ligand containing two or more, generally two, coordinating heteroatoms such as N, O, S, or P, with preferred such ligands being diimine ligands of the Brookhart type.
  • a bidentate or multidentate ligand containing two or more, generally two, coordinating heteroatoms such as N, O, S, or P, with preferred such ligands being diimine ligands of the Brookhart type.
  • One representative bidentate ligand has the structure of formula (VI)
  • R 15 , R 16 , R 17 , and R 18 hydrocarbyl e.g., Ci-C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 5 -C 24 aryl, C6-C 2 4 alkaryl, or C6-C 2 4 aralkyl
  • substituted hydrocarbyl e.g., substituted Ci-C 2 o alkyl, C 2 -C 2 o alkenyl, C 2 -C 2 o alkynyl, Cs-C 2 4 aryl, C6-C 2 4 alkaryl, or C6-C 2 4 aralkyl
  • heteroatom-containing hydrocarbyl e.g., Ci-C 2 o heteroalkyl, C5-C 2 4 heteroaryl, heteroatom-containing C6-C 2 4 aralkyl, or heteroatom-containing Ce- C 2 4 alkaryl
  • substituted heteroatom-containing hydrocarbyl e.
  • a bidentate ligand or a tridentate ligand examples include, but are not limited to, bisphosphines, dialkoxides, alkyldiketonates, and aryldiketonates.
  • Specific examples include -P(Ph) 2 CH 2 CH 2 P(Ph) 2 -, -As(Ph) 2 CH 2 CH 2 As(Ph 2 )-, -P(Ph) 2 CH 2 CH 2 C(CF 3 ) 2 0-, binaphtholate dianions, pinacolate dianions, -P(CH 3 ) 2 (CH 2 ) 2 P(CH 3 ) 2 -, and -OC(CH 3 ) 2 (CH 3 ) 2 CO-.
  • Preferred bidentate ligands are -P(Ph) 2 CH 2 CH 2 P(Ph) 2 - and -P(CH 3 ) 2 (CH 2 ) 2 P(CH 3 ) 2 -.
  • Tridentate ligands include, but are not limited to, (CH 3 ) 2 NCH 2 CH 2 P(Ph)CH 2 CH 2 N(CH 3 ) 2 .
  • tridentate ligands are those in which any three of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 (e.g., X 1 , L 1 , and L 2 ) are taken together to be cyclopentadienyl, indenyl, or fluorenyl, each optionally substituted with C 2 -C 2 o alkenyl, C 2 -C 2 o alkynyl, Ci-C 2 o alkyl, C 5 -C 2 o aryl, Ci-C 2 o alkoxy, C 2 -C 2 o alkenyloxy, C 2 -C 2 o alkynyloxy, C 5 -C 2 o aryloxy, C 2 -C 2 o alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl, or C1-C20 alkylsulfmyl,
  • X, L 1 , and L 2 are taken together to be cyclopentadienyl or indenyl, each optionally substituted with vinyl, C1-C10 alkyl, C5- C20 aryl, C1-C10 carboxylate, C2-C10 alkoxycarbonyl, C1-C10 alkoxy, or C5-C20 aryloxy, each optionally substituted with Ci-Ce alkyl, halide, Ci-Ce alkoxy or with a phenyl group optionally substituted with halide, Ci-Ce alkyl or Ci-Ce alkoxy.
  • X, L 1 and L 2 may be taken together to be cyclopentadienyl, optionally substituted with vinyl, hydrogen, methyl, or phenyl.
  • Tetradentate ligands include, but are not limited to 02C(CH2)2P(Ph)(CH2)2P(Ph)(CH2)2C02, phthalocyanines, and porphyrins.
  • M is a Group 8 transition metal, particularly Ru or Os, or, more particularly, Ru;
  • X 1 , X 2 , and L 1 are as previously defined herein for the first and second groups of catalysts
  • Y is a heteroatom selected from N, O, S, and P; preferably Y is O or N;
  • R 5 , R 6 , R 7 , and R 8 are each, independently, selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroatom containing alkenyl, heteroalkenyl, heteroaryl, alkoxy, alkenyloxy, aryloxy, alkoxycarbonyl, carbonyl, alkylamino, alkylthio, aminosulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonyl, nitrile, nitro, alkylsulfmyl, trihaloalkyl, perfluoroalkyl, carboxylic acid, ketone, aldehyde, nitrate, cyano, isocyanate, hydroxyl, ester, ether, amine, imine, amide, halogen- substituted amide, trifluoroamide, sulf
  • Z is a group selected from hydrogen, alkyl, aryl, functionalized alkyl, functionalized aryl where the functional group(s) may independently be one or more or the following: alkoxy, aryloxy, halogen, carboxylic acid, ketone, aldehyde, nitrate, cyano, isocyanate, hydroxyl, ester, ether, amine, imine, amide, trifluoroamide, sulfide, disulfide, carbamate, silane, siloxane, phosphine, phosphate, or borate; methyl, isopropyl, sec -butyl, t-butyl, neopentyl, benzyl, phenyl and trimethylsilyl; and wherein any combination or combinations of X 1 , X 2 , L ⁇ Y, Z, R 5 , R 6 , R 7 , and R 8 may be linked to a support. Additionally, R 5 , R 6 , R
  • L 1 , X 1 , X 2 , and M are as described for any of the other groups of catalysts.
  • Suitable chelating carbenes and carbene precursors are further described by Pederson et al. (U.S. Pat. Nos. 7,026,495 and 6,620,955, the disclosures of both of which are incorporated herein by reference) and Hoveyda et al. (U.S. Pat. No. 6,921,735 and WO0214376, the disclosures of both of which are incorporated herein by reference).
  • complexes having linked ligands include those having linkages between a neutral NHC ligand and an anionic ligand, a neutral NHC ligand and an alkylidine ligand, a neutral NHC ligand and an L 2 ligand, a neutral NHC ligand and an L 3 ligand, an anionic ligand and an alkylidine ligand, and any combination thereof. While the possible structures are too numerous to list herein, suitable structures based on formula (III) include:
  • transition metal carbene complexes include, but are not limited to: neutral ruthenium or osmium metal carbene complexes containing metal centers that are formally in the +2 oxidation state, have an electron count of 16, are penta-coordinated, and are of the general formula (IX);
  • M, X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 are as defined for any of the previously defined four groups of catalysts;
  • r and s are independently zero or 1 ;
  • t is an integer in the range of zero to 5;
  • k is an integer in the range of zero to 1 ;
  • Y is any non-coordinating anion (e.g., a halide ion, BF/f, etc.);
  • Z 3 is any cationic moiety such as -P(R 2 )3 + or -N(R 2 )3 + ;
  • any two or more of X 1 , X 2 , L 1 , L 2 , L 3 , Z 1 , Z 2 , Z 3 , R 1 , and R 2 may be taken together to form a cyclic group, e.g., a multidentate ligand, and wherein any one or more of X 1 , X 2 , L 1 , L 2 , L 3 , Z 1 , Z 2 , Z 3 , R 1 , and R 2 may be attached to a support.
  • M is a Group 8 transition metal, particularly ruthenium or osmium, or more particularly, ruthenium;
  • X 1 , X 2 , L 1 and L 2 are as defined for the first and second groups of catalysts defined above;
  • R G1 , R G2 , R G3 , R G4 , R G5 , and R G6 are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroatom containing alkenyl,
  • R G7 , R G8 , R G9 , R G1 °, R GU , R G12 , R G13 , R G14 , R G15 and R G16 are as defined above for R G1 , R G2 , R G3 , R G4 , R G5 , and R G6 for Group 8 transition metal complex of formula XIII or any one or more of the R G7 , R G8 , R G9 , R G1 °, R GU , R G12 , R G13 , R G14 , R G15 and R G16 may be linked together to form a cyclic group, or any one or more of the R G7 , R G8 , R 09 , R G1 °, R GU , R G12 , R G13 , R G14 , R G15 and R G16 may be attached to a support.
  • Group 8 transition metal complex of formula XIII is a Group 8 transition metal complex of formula (XV):
  • olefin metathesis catalysts that may be used in the invention disclosed herein, is a Group 8 transition metal complex comprising a Schiff base ligand having the structure of formula (XVI):
  • M is a Group 8 transition metal, particularly ruthenium or osmium, or more particularly, ruthenium;
  • X 1 , and L 1 are as defined for the first and second groups of catalysts defined above;
  • Z is selected from the group consisting of oxygen, sulfur, selenium, NR JU , PR JU , AsR JU , and SbR JU ;
  • R J1 , R J2 , R J3 , R J4 , R J5 , R J6 , R J7 , R J8 , R J9 , R J1 °, and R JU are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroatom containing alkenyl, heteroalkenyl, heteroaryl, alkoxy, alkenyloxy, aryloxy, alkoxycarbonyl, carbonyl, alkylamino, alkylthio, aminosulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonyl, nitrile, nitro, alkylsulfinyl, trihaloalkyl, perfluoroalkyl, carboxylic acid, ketone, aldehyde, nitrate, cyano, isocyanate
  • Group 8 transition metal complex of formula (XVI) is a Group 8 transition metal complex comprising a Schiff base ligand having the structure of formula (XVII):
  • R J12 , R J13 , R J14 , R J15 , R J16 , R J17 , R J18 , R J19 , R J2 °, and R J21 are as defined above for R J1 , R J2 , R J3 , R J4 , R J5 , and R J6 for Group 8 transition metal complex of fonnula XVI, or any one or more of the R J7 , R J8 , R J9 , R J1 °, R jn , R 112 , R 113 , R J14 , R J15 , R 6 , R 117 , R J18 , R J19 , R J20 , and R J21 may be linked together to form a cyclic group, or any one or more of the R J7 , R J8 , R '19 , R J1 °, R i , R J12 , R J13 , R JM , R '115 , R J16
  • Group 8 transition metal complex of formula (XVI) is a Group 8 transition metal complex comprising a Schiff base ligand having the structure of formula (XVIII):
  • olefin metathesis catalysts that may be used in the invention disclosed herein, is a Group 8 transition metal complex comprising a Schiff base ligand having the structure of formula (XIX):
  • M is a Group 8 transition metal, particularly ruthenium or osmium, or more particularly, ruthenium;
  • X 1 , L 1 , R 1 , and R 2 are as defined for the first and second groups of catalysts defined above;
  • Z is selected from the group consisting of oxygen, sulfur, selenium, NR K5 , PR K5 , AsR K5 , and
  • R K1 , R K2 , R K3 , R K4 , and R K5 are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroatom containing alkenyl,
  • catalysts of formulas (XVI) to (XIX) may be optionally contacted with an activating compound, where at least partial cleavage of a bond between the Group 8 transition metal and at least one Schiff base ligand occurs, wherein the activating compound is either a metal or silicon compound selected from the group consisting of copper (I) halides; zinc compounds of the formula Zn(R Y1 )2, wherein R Y1 is halogen, C1-C7 alkyl or aryl; tin compounds represented by the formula
  • R Y2 , R Y3 , R Y4 and R Y5 is independently selected from the group consisting of halogen, C1-C20 alkyl, C3-C10 cycloalkyl, aryl, benzyl and C2-C7 alkenyl; and silicon compounds represented by the formula SiR Y6 R Y7 R Y8 R Y9 wherein each of R Y6 , R Y7 , R Y8 , R Y9 is independently selected from the group consisting of hydrogen, halogen, C1-C20 alkyl, halo, C1-C7 alkyl, aryl, heteroaryl, and vinyl.
  • catalysts of formulas (XVI) to (XIX) may be optionally contacted with an activating compound where at least partial cleavage of a bond between the Group 8 transition metal and at least one Schiff base ligand occurs, wherein the activating compound is an inorganic acid such as hydrogen iodide, hydrogen bromide, hydrogen chloride, hydrogen fluoride, sulfuric acid, nitric acid, iodic acid, periodic acid, perchloric acid, HOCIO, HOCIO2 and HOIO3.
  • an activating compound is an inorganic acid such as hydrogen iodide, hydrogen bromide, hydrogen chloride, hydrogen fluoride, sulfuric acid, nitric acid, iodic acid, periodic acid, perchloric acid, HOCIO, HOCIO2 and HOIO3.
  • catalysts of formulas (XVI) to (XIX) may be optionally contacted with an activating compound where at least partial cleavage of a bond between the Group 8 transition metal and at least one Schiff base ligand occurs, wherein the activating compound is an organic acid such as sulfonic acids including but not limited to methanesulfonic acid, aminobenzenesulfonic acid, benzenesulfonic acid, napthalenesulfonic acid, sulfanilic acid and trifluoromethanesulfonic acid; monocarboxylic acids including but not limited to acetoacetic acid, barbituric acid, bromoacetic acid, bromobenzoic acid, chloroacetic acid, chlorobenzoic acid, chlorophenoxyacetic acid, chloropropionic acid, cis-cinnamic acid, cyanoacetic acid, cyanobutyric acid, cyanophenoxyacetic acid, cyanopropionic acid, dichloroacetic
  • Non-limiting examples of catalysts that may be used to prepare supported complexes and in the reactions disclosed herein include the following, some of which for convenience are identified throughout this disclosure by reference to their molecular weight:
  • Ph represents phenyl
  • Cy represents cyclohexyl
  • Cp represents cyclopentyl
  • Me represents methyl
  • Bu represents n-butyl
  • t-Bu represents tert- butyl
  • z ' -Pr represents isopropyl
  • py represents pyridine (coordinated through the N atom)
  • Mes represents mesityl (i.e., 2,4,6-trimethylphenyl)
  • DiPP and DIPP represents 2,6-diisopropylphenyl
  • MiPP respresents 2-isopropylphenyl.
  • catalysts useful to prepare supported complexes and in the reactions disclosed herein include the following: ruthenium (II) dichloro (3-methyl-2-butenylidene) bis(tricyclopentylphosphine) (C716); ruthenium (II) dichloro (3-methyl-2-butenylidene)
  • Still further catalysts useful in ROMP reactions, and/or in other metathesis reactions, such as ring-closing metathesis, cross metathesis, ring-opening cross metathesis, self-metathesis, ethenolysis, alkenolysis, acyclic diene metathesis polymerization, and combinations thereof, include the following structures:
  • transition metal complexes used as catalysts herein can be prepared by several different methods, such as those described by Schwab et al. (1996) J. Am. Chem. Soc. 1 18: 100- 110. Scholl et al. (1999) Org. Lett. 6:953-956, Sanford et al. (2001) J. Am. Chem. Soc. 123:749-750, U.S. Pat. No. 5,312,940, and U.S. Pat. No. 5,342,909, the disclosures of each of which are incorporated herein by reference. Also see U.S. Pat. Pub. No. 2003/0055262 to Grubbs et al., WO 02/079208, and U.S. Pat. No. 6,613,910 to Grubbs et al., the disclosures of each of which are incorporated herein by reference.
  • Preferred metal carbene olefin metathesis catalysts are Group 8 transition metal complexes having the structure of formula (I) commonly called “First Generation Grubbs” catalysts, formula (III) commonly called “Second Generation Grubbs” catalysts, or formula (VII) commonly called “Grubbs- Hoveyda” catalysts.
  • More preferred metal carbene olefin metathesis catalysts have the structure of formula (I)
  • M is a Group 8 transition metal
  • L 1 , L 2 , and L 3 are neutral electron donor ligands
  • n 0 or 1 ;
  • n 0,1, or 2;
  • k is 0 or 1 ;
  • X 1 and X 2 are anionic ligands
  • R 1 and R 2 are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups,
  • any two or more of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 can be taken together to form one or more cyclic groups, and further wherein any one or more of X 1 , X 2 , L 1 , L 2 , L 3 , R 1 , and R 2 may be attached to a support; and formula (VII)
  • M is a Group 8 transition metal
  • L 1 is a neutral electron donor ligand
  • X 1 and X 2 are anionic ligands
  • Y is a heteroatom selected from O or N;
  • R 6 , R 7 , and R 8 are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups; n is 0,1, or 2; and
  • Z is selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups,
  • any combination of Y, Z, R 5 ,R 6 , R 7 , and R 8 can be linked to form one or more cyclic groups, and further wherein any combination of X 1 , X 2 , L 1 , Y, Z, R 5 ,R 6 , R 7 , and R 8 may be attached to a support.
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PlVfePh), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isoprop
  • PCy3 tricyclohexylphosphine
  • P-i-P ⁇ triisopropylphosphine
  • PPI13 triphenylphosphine
  • PMePli2 methyldiphenylphosphine
  • PMe2Ph dimethylphenylphosphine
  • PEt 2 Ph diethylphenylphosphine
  • X 1 and X 2 are chloride:
  • M is ruthenium
  • L 1 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine (Pn- BU3), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine ( ⁇ -1- ⁇ 3), triphenylphosphine (PPli3), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PVfePh), and diethylphenylphosphine (PEt2Ph); or L 1 is an N- heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, l,3-bis(2,4,6- trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropylphenyl
  • X 1 and X 2 are chloride:
  • Y is oxygen
  • R 5 , R 6 , R 7 , and R 8 are each hydrogen
  • n 1 ;
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropyl
  • PCV3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • methyldiphenylphosphine (PMePh 2 ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph);
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropyl
  • PCy3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • methyldiphenylphosphine (PMePh 2 ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph);
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine ( ⁇ -1- ⁇ 3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePli2), dimethylphenylphosphine (PlVfePh), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropy
  • PCy3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPI13 triphenylphosphine
  • methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PlVfePh), and diethylphenylphosphine (PEt 2 Ph);
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PlVfePh), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isoprop
  • PCy3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPI13 triphenylphosphine
  • PMePli2 methyldiphenylphosphine
  • PMe2Ph dimethylphenylphosphine
  • PEt 2 Ph diethylphenylphosphine
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh 2 ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phosphin
  • PCV3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt 2 Ph);
  • X 1 and X 2 are chloride
  • R 1 and R 2 are taken together to form an indenylidene moiety.
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phos
  • PCV3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • methyldiphenylphosphine (PMePh 2 ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph);
  • X 1 and X 2 are chloride
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentyl
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PlVfePh), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopent
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPli3), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphos
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylpho
  • X 1 and X 2 are chloride
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentyl
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PlVfePh), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopent
  • X 1 and X 2 are chloride
  • M is ruthenium
  • L 1 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine (Pn- BU3), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine ( ⁇ -1- ⁇ 3), triphenylphosphine (PPh3), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N- heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, l,3-bis(2,4,6- trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropylphenyl)-2
  • X 1 and X 2 are chloride
  • Y is oxygen
  • R 5 , R 6 , R 7 , and R 8 are each hydrogen
  • n 1 ;
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropyl
  • PCV3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • methyldiphenylphosphine (PMePh 2 ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph);
  • X 1 and X 2 are chloride
  • Pv 1 is hydrogen and R 2 is phenyl or or thienyl.
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phos
  • PCy3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • PMePh 2 methyldiphenylphosphine
  • PMe 2 Ph dimethylphenylphosphine
  • PEt 2 Ph diethylphenylphosphine
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentyl
  • X 1 and X 2 are chloride
  • Pv 1 is hydrogen and R 2 is phenyl or or thienyl.
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphme (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphos
  • X 1 and X 2 are chloride
  • Pv 1 is hydrogen and R 2 is phenyl or or thienyl.
  • R 2 is phenyl or or thienyl.
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropyl
  • PCV3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • methyldiphenylphosphine (PMePh 2 ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph);
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphme (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted pho
  • PCV3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPli3 triphenylphosphine
  • PMePl ⁇ methyldiphenylphosphine
  • PMe 2 Ph dimethylphenylphosphme
  • PEt 2 Ph diethylphenylphosphine
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPli3), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphme (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopent
  • X 1 and X 2 are chloride
  • M is ruthenium
  • n 0;
  • n 0;
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr 3 ), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphos
  • X 1 and X 2 are chloride
  • M is ruthenium
  • X 1 and X 2 are chloride
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh 2 ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, 1,3- bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, l,3-bis(2,6-di-isopropylphen
  • PCys tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • Ph3 triphenylphosphine
  • methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PlVfePh), and diethylphenylphosphine (PEt 2 Ph).
  • M is ruthenium
  • X 1 and X 2 are chloride
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from the group consisting of l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phos
  • PCy3 tricyclohexylphosphine
  • P-i-Pr3 triisopropylphosphine
  • PPI13 triphenylphosphine
  • PMePh2 methyldiphenylphosphine
  • PlVfePh dimethylphenylphosphine
  • PEt 2 Ph diethylphenylphosphine
  • M is ruthenium
  • X 1 and X 2 are chloride
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCV3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PMe 2 Ph), and diethylphenylphosphine (PEt 2 Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphos
  • M is ruthenium
  • X 1 and X 2 are chloride
  • L 1 and L 2 are trisubstituted phosphines independently selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), triphenylphosphine (PPI13), methyldiphenylphosphine (PMePl ⁇ ), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph); or L 1 is an N-heterocyclic carbene selected from l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, and L 2 is a trisubstituted phosphine selected from the group consisting of tri-n-butylphosphine ( ⁇ - ⁇ 3 ⁇ 4), tricyclopentylpho
  • Suitable supports for any of the catalysts described herein may be of synthetic, semisynthetic, or naturally occurring materials, which may be organic or inorganic, e.g., polymeric, ceramic, or metallic. Attachment to the support will generally, although not necessarily, be covalent, and the covalent linkage may be direct or indirect. Indirect covalent linkages are typically, though not necessarily, through a functional group on a support surface. Ionic attachments are also suitable, including combinations of one or more anionic groups on the metal complexes coupled with supports containing cationic groups, or combinations of one or more cationic groups on the metal complexes coupled with supports containing anionic groups.
  • suitable supports may be selected from silicas, silicates, aluminas, aluminum oxides, silica-aluminas, aluminosilicates, zeolites, titanias, titanium dioxide, magnetite, magnesium oxides, boron oxides, clays, zirconias, zirconium dioxide, carbon, polymers, cellulose, cellulosic polymers amylose, amylosic polymers, or a combination thereof.
  • the support preferably comprises silica, a silicate, or a combination thereof.
  • a support that has been treated to include functional groups, inert moieties, and/or excess ligands. Any of the functional groups described herein are suitable for incorporation on the support, and may be generally accomplished through techniques known in the art. Inert moieties may also be incorporated on the support to generally reduce the available attachment sites on the support, e.g., in order to control the placement, or amount, of a complex linked to the support.
  • the catalyst compositions comprising at least one metal carbene olefin metathesis catalyst may be utilized in olefin metathesis reactions according to techniques known in the art.
  • the catalyst compositions comprising at least one metal carbene olefin metathesis catalyst are typically added to the resin composition as a solid, a solution, or as a suspension.
  • the at least one metal carbene olefin metathesis catalyst is suspended in a dispersing carrier such as mineral oil, paraffin oil, soybean oil, tri-isopropylbenzene, or any hydrophobic liquid which has a sufficiently high viscosity so as to permit effective dispersion of the catalyst(s), and which is sufficiently inert and which has a sufficiently high boiling point so that is does not act as a low-boiling impurity in the olefin metathesis reaction.
  • a dispersing carrier such as mineral oil, paraffin oil, soybean oil, tri-isopropylbenzene, or any hydrophobic liquid which has a sufficiently high viscosity so as to permit effective dispersion of the catalyst(s), and which is sufficiently inert and which has a sufficiently high boiling point so that is does not act as a low-boiling impurity in the olefin metathesis reaction.
  • the amount of catalyst that is used i.e., the "catalyst loading" in the reaction is dependent upon a variety of factors such as the identity of the reactants and the reaction conditions that are employed. It is therefore understood that catalyst loading may be optimally and independently chosen for each reaction. In general, however, the catalyst will be present in an amount that ranges from a low of about 0.1 ppm, 1 ppm, or 5 ppm, to a high of about 10 ppm, 15 ppm, 25 ppm, 50 ppm, 100 ppm, 200 ppm, 500 ppm, or 1000 ppm relative to the amount of an olefinic substrate.
  • the catalyst will generally be present in an amount that ranges from a low of about
  • 0.00001 mol%, 0.0001 mol%, or 0.0005 mol% to a high of about 0.001 mol%, 0.0015 mol%, 0.0025 mol%, 0.005 mol%, 0.01 mol%, 0.02 mol%, 0.05 mol%, or 0.1 mol% relative to the olefmic substrate.
  • the catalyst When expressed as the molar ratio of monomer to catalyst, the catalyst (the "monomer to catalyst ratio"), loading will generally be present in an amount that ranges from a low of about
  • Resin compositions of the present invention comprise a cyclic olefin composition.
  • a resin composition according to the present invention comprises a cyclic olefin composition, wherein the cyclic olefin composition comprise 10.0 mol% to 80.0 mol% of at least one cyclic olefin containing multiunsaturation, and up to 90.0 mol% of at least one cyclic olefin containing monounsaturation, wherein the at least one cyclic olefin containing multiunsaturation may be substituted or unsubstituted, and wherein the at least one cyclic olefin containing monounsaturation may be substituted or unsubstituted, and wherein the substituents are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom- containing hydrocarbyl, -(Z * ) n -Fn where n is
  • resin compositions of the invention may also comprise at least one substrate material.
  • resin compositions according to the invention may also comprise at least one adhesion promoter, where the resin composition is combined with a catalyst composition comprising at least one olefin metathesis catalyst to form a ROMP composition, and the resulting ROMP composition is applied to at least one substrate material.
  • resin compositions according to the invention may also comprise a cyclic olefin composition and at least one adhesion promoter comprising at least one compound containing at least two isocyanate groups, where the resin composition is combined with at least one olefin metathesis catalyst, and the resulting ROMP composition is applied to at least one substrate material, wherein the substrate material may be functionalized substrate material, such as, for example, a heteroatom-functionalized substrate, such as, for example, an amino-functionalized substrate.
  • resin compositions according to the invention may also comprise at least one adhesion promoter comprising at least one compound containing at least two isocyanate groups, where the resin composition is combined with at least olefin metathesis catalyst, and the resulting resin composition is applied to at least one substrate material, such as, for example, a glass substrate material or carbon substrate material.
  • resin compositions, particularly ROMP compositions according to the invention comprise at a cyclic olefin composition, at least one olefin metathesis catalyst, at least one adhesion promoter comprising at least one compound containing at least two isocyanate groups, and at least one heteroatom-functionalized substrate material.
  • the amounts of the adhesion promoter in the resin composition may vary over a wide range and may vary depending on the manufacturing operation or the particular end-use application. Generally, any level of adhesion promoter which produces a desired increase in mechanical properties is of particular interest.
  • the concentration of the adhesion promoter typically ranges from 0.001-50 phr, particularly 0.05- 10 phr, more particularly 0.1-10 phr, or even more particularly 0.5-4.0 phr.
  • substrate materials may advantageously comprise an aminosilane -treated substrate.
  • resin compositions according to the invention may additionally comprise an exogenous inhibitor.
  • Exogenous inhibitors or "gel modification additives”, for use in the present invention are disclosed in U.S. Pat. No. 5,939,504, the contents of which are incorporated herein by reference.
  • resin compositions according to the invention may additionally comprise a hydroperoxide gel modifier. Hydroperoxide gel modifiers (e.g. cumene hydroperoxide) for use in the present invention are disclosed in International Pat. App. No. PCT/US2012/042850.
  • the resin compositions according to the invention may additionally comprise an adhesion promoter.
  • Adhesion promoters for use in the present invention are disclosed in International Pat. App. No. PCT/US2012/042850.

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Abstract

La présente invention a pour objet de traiter un ou plusieurs problèmes susmentionnés et se rapporte à des matériaux d'isolation thermique et à des compositions de matériaux d'isolation thermique ainsi qu'à des procédés pour isoler thermiquement des pipelines et un équipement associé, des structures et des objets utilisés lors d'un forage en mer. La présente invention a pour objet des articles manufacturés comprenant les matériaux d'isolation thermique et/ou les compositions de matériaux d'isolation thermique de l'invention. Plus particulièrement, la présente invention se rapporte à l'utilisation de polymères de polymérisation par métathèse par ouverture de cycle (polymères ROMP) et/ou des composites de polymères ROMP pour isoler thermiquement des pipelines et un équipement associé, des structures et des objets utilisés lors d'un forage pétrolier en mer.
PCT/US2014/072198 2013-06-24 2014-12-23 Isolation thermique WO2015134095A1 (fr)

Priority Applications (1)

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US15/122,860 US10711090B2 (en) 2013-06-24 2014-12-23 Thermal insulation

Applications Claiming Priority (4)

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US201461948196P 2014-03-05 2014-03-05
US61/948,196 2014-03-05
USPCT/US14/043968 2014-06-24
PCT/US2014/043968 WO2014210076A1 (fr) 2013-06-24 2014-06-24 Isolation thermique

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3199577A1 (fr) * 2016-02-01 2017-08-02 Telene SAS Procédé de préparation d'un article à deux composants et article obtenu par le procédé
US9896527B2 (en) 2016-03-01 2018-02-20 Saudi Arabian Oil Company Highly selective polynorbornene homopolymer membranes for natural gas upgrading

Citations (3)

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Publication number Priority date Publication date Assignee Title
US20070037946A1 (en) * 2003-01-31 2007-02-15 Tomoo Sugawara Process for producing cycloolefin resin film and process for producing cycloolefin polymer sheet or film
US20070060730A1 (en) * 2005-08-26 2007-03-15 Korea Kumho Petrochemical Co., Ltd./New Korea Inte Method of preparing cyclic olefin copolymer having controlled gel contents
US20120058332A1 (en) * 2010-09-03 2012-03-08 Basf Se Barrier coating made of cycloolefin copolymers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070037946A1 (en) * 2003-01-31 2007-02-15 Tomoo Sugawara Process for producing cycloolefin resin film and process for producing cycloolefin polymer sheet or film
US20070060730A1 (en) * 2005-08-26 2007-03-15 Korea Kumho Petrochemical Co., Ltd./New Korea Inte Method of preparing cyclic olefin copolymer having controlled gel contents
US20120058332A1 (en) * 2010-09-03 2012-03-08 Basf Se Barrier coating made of cycloolefin copolymers

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3199577A1 (fr) * 2016-02-01 2017-08-02 Telene SAS Procédé de préparation d'un article à deux composants et article obtenu par le procédé
WO2017134073A1 (fr) * 2016-02-01 2017-08-10 Telene Sas Procédé de préparation d'un article à deux composants et article pouvant être obtenu par le procédé
CN108713036A (zh) * 2016-02-01 2018-10-26 特灵公司 用于制备双组分制品的方法和可通过该方法获得的制品
US11155010B2 (en) 2016-02-01 2021-10-26 Telene Sas Method for preparing a two-component article and article obtainable by the method
US9896527B2 (en) 2016-03-01 2018-02-20 Saudi Arabian Oil Company Highly selective polynorbornene homopolymer membranes for natural gas upgrading

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